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Theoretical Development of the CD spectroscopic Method and Application to Bio-organic Science

Research Project

Project/Area Number 07408032
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionTohoku University

Principal Investigator

HARADA Nobuyuki  Inst.for Chem.React.Sci., Tohoku University, Professor, 反応化学研究所, 教授 (30006324)

Co-Investigator(Kenkyū-buntansha) YOSHIDA Akihiro  Inst.for Chem.React.Sci., Tohoku University, Research Associate, 反応化学研究所, 助手 (10292301)
Project Period (FY) 1995 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥6,200,000 (Direct Cost: ¥6,200,000)
Fiscal Year 1998: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1997: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1996: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsCD Exciton Method / Enantioresolution / Absolute Configuration / X-ray Crystallographic Analysis / Split Cotton Effects / Biflavone / CD Auxiliary / Conformational Analysis / CDスペクトル / 1,1-ビフェナンスリル / 絶対立体化学 / 不斉補助基 / キラルジクロロフタル酸法 / 単一官能基化合物 / 励起子相互作用 / 円二色性スペクトル / 励起子キラリティー法 / ねじれたパイ電子共役系 / 新規不斉補助基 / シガトキシン / 天然アトロープ異性体 / キラルフタル酸法 / 鎖状1, 2-ジオール / 13Cサテライトパンド法 / ねじれたパイ電子系 / カンファーサルタム法 / 結晶化不斉認識 / キラルフタル酸アミド法 / 鎖状1,2-グリュコール
Research Abstract

(1). Chiral Phthalic Acid Amide, a Chiral Auxiliary Useful for Enantiomer Resolution and X-Ray Crystallographic Determination of the Absolute Stereochemistry of Alcohols.
(2). A CD Method for Determination of the Absolute Stereochemistry of Acyclic Glycols. 2. Application of the CD Exciton Chirality Method to Acyclic 1,2-Dibenzoates Systems.
(3). The CD Exciton Chirality Method and Benzoylation of Sterically Hindered alpha-Glycol by Trans-Esterification : Forskolin Case.
(4). Lipase-Catalyzed Kinetic Resolution of Cyclobutylmethanols and Determination of Absolute Stereochemistry by X-Ray Analysis.
(5). Enantioresolution and Absolute Stereochemistry of 3,3'-DiacetyI-4,4', 6,6'-tetramethoxy- 2,2'-biphenyldiol.
(6). Total Synthesis and Absolute Stereochemistry of Natural Atropisomer of Biflavone, [CD(+)362.0]-(-)4', 4''', 7,7"-Tetra-O-methylcupressuflavone.
(7). Application of the CD Exciton Chirality Method to Chiral 1,2-Diamines. Use of C2v-symmetrical 2,3-Naphthalenedicarboximido Chromophore … More .
(8). Enantioresolution and Absolute Stereochemistry of 2-(l-Naphthyl)propane-l, 2-diol and Related Compounds. The method using chiral phthalic acid amides was applied to make the enantioresolution of 2-(l-naphthyl)propane-l, 2-diol giving enantiopure (-)-diol, the S absolute configuration of which was unambiguously determined by X-ray crystallography of its (-)-p-bromobenzoate. The S absolute configurations of (+)-2-methoxy-2-(1-naphthyl)propionic acid and related compounds were also determined by chemical correlation to (S)-(-)-diol.
(9). New Strategy for Determining the Absolute Stereochemistry of Mono-Functional Compounds by the CD Exciton Chirality Method. The CD exciton chirality method has been extensively applied to various natural products and chiral synthetic compounds to determine their absolute configurations in a nonempirical manner. However, application of the CD exciton chirality method has been limited to chiral compounds with two or more functional groups, because exciton CD Cotton effects are observable only for the interaction between two or more chromophores. This has been a weak point of the CD exciton chirality method, and therefore it has never been applied to mono-functional chiral compounds. We reported a new strategy for determining the absolute configuration of mono-fucntional compounds by the CD exciton chirality method. Less

Report

(5 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • 1996 Annual Research Report
  • 1995 Annual Research Report
  • Research Products

    (118 results)

All Other

All Publications (118 results)

  • [Publications] N.Harada: "Chiral Phthalic Acid Amide, a Chiral Auxiliary Useful for Enantiomer Resolution and X-Ray Crystallographic Determination of the Absolute Stereochemistry of Alcohols." Enantiomer. 1. 35-39 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Mimaki, N.Harada: "A New Furostanol Saponin with Six Sugars from the Bulbs of Allium sphaerosephalon Structural Elucidation by Modern NMR Techniques." Chem.Lett.431-432 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "A CD Method for Determination of the Absolute Stereochemistry of Acyclic Glycols. 2. Application of the CD Exciton Chirality Method to Acyclic 1, 2-Dibenzoates Systems." Enantiomer. 1. 119-138 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Absolute Stereochemistry of [6. 6] Vespirene Family Compounds as Determined by the X-Ray Crystallography." Enantiomer. 1. 115-118 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "The Recent Advances in the Spectroscopy of Circular Dichroism (CD) and Its Application for Chiral Organic Compounds." Zhurn.Org.Khim.32. 167-179 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "CD Data Instead of [α]_D Values." Enantiomer. 1. 81-82 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Sugioka, N.Harada: "The CD Exciton Chirality Method and Benzoylation of Sterically Hindered α-Glycol by Trans-Esterification : Forskolin Case." Enantiomer. 2. 117-121 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Synthesis, Circular Dichroism, and Absolute Stereochemistry of 1, 1' : 4', 1"-Ternaphthalene" Chirality. 6. 623-625 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Absolute Configuration and Conformation of 1, 1' : 4', 1"-Ternaphthalene Compounds as Determined by X-Ray Crystallography." Enantiomer. 2. 123-126 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Chiral Dichlorophthalic Acid Amide, an Improved Chiral Auxiliary Useful for Enantioresolution and X-Ray Crystallographic Determination of Absolute Stereochemistry." Enantiomer. 2. 303-309 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Nemoto, N.Harada: "Lipase-Catalyzed Kinetic Resolution of Cyclobutylmethanols and Determination of Absolute Stereochemistry by X-Ray Analysis." Enantiomer. 2. 127-131 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "NMR^<13>C Satellite Signals Useful for the First-Order Analysis of Complex Spin Systems." Enantiomer. 2. 349-352 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Chemistry of Unique Chiral Olefins. 1. Synthesis, Enantioresolution, Circular Dichroism, and Theoretical Determination of the Absolute Stereochemistry of trans-and cis-1, 1', 2, 2', 3, 3', 4, 4'-Octahydro-4, 4'-biphenanthrylidenes." J.Am.Chem.Soc.119. 7241-7248 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Chemistry of Unique Chiral Olefins. 2. Unexpected Thermal Racemization of cis- 1,1', 2, 2', 3, 3', 4, 4'-Octahydro-4, 4'-biphenanthrylidenes." J.Am.Chem.Soc.119. 7249-7255 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Chemistry of Unique Chiral Olefins. 3. Synthesis and Absolute Stereochemistry of trans-and cis-1, 1', 2, 2', 3, 3', 4, 4'-Octahydro-3, 3'-dimethyl-4, 4'-biphenanthrylidenes." J.Am.Chem.Soc.119. 7256-7264 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Enantioresolution and Absolute Stereochemistry of 3, 3'-Diacetyl-4, 4', 6, 6'-tetramethoxy-2, 2'-biphenyldiol" Enantiomer. 2. 353-358 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Watanabe, N.Harada: "A Convenient Synthesis of (1S, 5S) -4-Alkyl-3-carbomethoxy-6, 6-dimethylbicyclo[3. 1. 1]-hept-3-en-2-ones with Highly Optical Purity." J.Org.Chem.62. 2992-2995 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] J.-G.Dong, N.Harada: "Theoretical Calculation of Circular Dichroic Excition-Split Spectra in Presence of Three Interactiong 2-Naphthoate Chromophores." Enantiomer. 2. 397-409 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.-Y.Li, N.Harada: "Total Synthesis and Absolute Stereochemistry of Natural Atropisomer of Biflavone, [CD(+)362.0]-(-)-4', 4''', 7, 7''-Tetra-O-methylcupressuflavone." J.Org.Chem.62. 7222-7227 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Enantioresolution and Absolute Stereochemistry of Diarylmethanols." Enantiomer. 2. 359-366 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Satake, N.Harada: "The Absolute Configuration of Ciguatoxin." J.Am.Chem.Soc.119. 11325-11326 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 原田宣之: "旋光度" 化学. 52. 48-49 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Molecular Chirality by Isotopic Substitution. Synthesis, Absolute Configuration, and CD Spectra of Chiral Diphenylmethanols." Enantiomer. 3. 64-70 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Watanabe, N.Harada: "Application of the CD Exciton Chirality Method to Chiral 1, 2-Diamines. Use of C_<2v>-symmetrucal 2, 3-Naphthalenedicarboximido Chromophore." Enantiomer. 3. 197-202 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Koumura, N.Harada: "X-Ray Crystallographic Determination of the Stereochemistry of a Unique Chiral Olefin, [CD(-)238.0]-(3R, 3'R)-(P, P)-(Z)-(+)-1, 1', 2, 2', 3, 3', 4, 4'-Octahydro-3, 3'-dimethyl-4, 4'-biphenanthrylidene." Enantiomer. 3. 251-253 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Ono, N.Harada: "Synthesis, Circular Dichroism, and Absolute Stereochemistry of a Chiral Spiroaromatic, [CD(+)335.8]-(R)-15, 15'-Spirobi [15H-indeno [1, 2-b] naphthacene]." Enantiomer. 3. 245-250 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Goto, N.Harada: "Absolute Configuration of Chiral Fullerenes and Covalent Derivatives from Their Calculated Circular Dichroism." J.Chem.Soc., perkin 2. 1719-1723 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Hattori, N.Harada: "Is the CD Exciton Chirality Method Applicable to Chiral 1, 1'-Biphenanthryl Compounds?" J.Am.Chem.Soc.120. 9086-9087 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Koumura, N.Harada: "Photochemistry and Absolute Stereochemistry of Unique Chiral Olefins, trans-and cis-1, 1', 2, 2', 3, 3', 4, 4'-Octahydro-3, 3'-dimethyl-4, 4'-biphenanthrylidenes." Chem Lett.1151-1152 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 原田宣之: "コットン効果" 化学. 54, ♯2. 51-53 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] R.W.J.Zijlstra, N.Harada: "Chemistry of Unique Chiral Olefins. Part4. Theoretical Studies of the Racemization Mechanism of trans-and cis-1, 1', 2, ', 3, 3', 4, 4'-Octahydro-4, 4'-biphenanthrylidenes." J.Org.Chem.in press. (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Kuwahara, N.Harada: "Enantioresolution and Absolute Stereochemistry of 2-(1-Naphthyl) propane-1, 2-diol and Related Compounds." Enantiomer. in press. (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "‘Circular Dichroism Spectroscopy and Absolute Stereochemistry of Biologically Active Compounds, 'in R. Cooper and J.K.Snyder, Ed., “Advanced Bioorganic Chemistry″" Marcel Dekker, Inc., New York, in press (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, T.Nehira, T.Soutome, N.Hiyoshi, and F.Kido: "Chiral Phthalic Acid Amide, a Chiral Auxiliary Useful for Enantiomer Resolution and X-Ray Crystallographic Determination of the Absolute Stereochemistry of Alcohols." Enantiomer. 1. 35-39 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Mimaki, T.Satou, M.Kuroda, A.Kameyama, Y.Sashida, H.-Y.Li, and N.Harada: "A New Furostanol Saponin with Six Sugars from the Bulbs of Allium sphaerosephalon Structural Elucidation by Modern NMR Techniques." Chem Lett.431-432 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, A.Saito, H.Ono, S.Murai, H.-Y.Li, J.Gawronski, K.Gawronska, T.Sugioka, and H.Uda: "A CD Method for Determination of the Absolute Stereochemistry of Acyclic Glycols. 2.Application of the CD Exciton Chirality Method to Acyclic 1,2-Dibenzoates Systems." Enantiomer. 1. 119-138 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, and H.Ono: "Absolute Stereochemistry of [6.6] Vespirene Family Compounds as Determined by the X-Ray Crystallography" Enantiomer. 1. 115-118 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "The Recent Advances in the Spectroscopy of Circular Dichroism (CD) and Its Application for Chiral Organic Compounds" Zhurn.Org.Khim.32. 167-179 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "CD Data Instead of [alpha]_D Values." Enantiomer. 1. 81-82 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Sugioka, N.Harada, H.Ehara, T.Soutome, and T.Kuriki: "The CD Exciton Chirality Method and Benzoylation of Sterically Hindered alpha-Glycol by Trans-Esterification : Forskolin Case." Enantiomer. 2. 117-121 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, N.Hiyoshi, V.P.Vassilev, and T.Hayashi: "Synthesis, Circular Dichroism, and Absolute Stereochemistry of 1,1' : 4', 1"-Ternaphthalene Compounds" Chirality. 9. 623-625 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, V.P.Vassilev, and N.Hiyoshi: "Absolute Configuration and Conformation of 1,1' : 4', 1"-Ternaphthalene Compounds as Determined by X-Ray Crystallography." Enantiomer. 2. 123-126 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, N.Koumura, and M.Robillard: "Chiral Dichlorophthalic Acid Amide, an Improved Chiral Auxiliary Useful for Enantioresolution and X-Ray Crystallographic Determination of Absolute Stereochemistry" Enantiomer. 2. 303-309 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Nemoto, J.Miyama, K.Fukumoto, H.Ehara, N.Harada, H.Uekusa, and Y.Ohashi: "Lipase-Catalyzed Kinetic Resolution of Cyclobutylmethanols and Determination of Absolute Stereochemistry by X-Ray Analysis" Enantiomer. 2. 127-131 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, H.-Y.Li, N.Koumura, T.Abe, M.Watanabe, and M.Hagiwara: "NMR ^<13>C Satellite Signals Useful for the First-Order Analysis of Complex Spin Systems." Enantiomer. 2. 349-352 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, A.Saito, N.Koumura, H.Uda, B.de Lange, W.F.Jager, H.Wynberg, and B.L.Feringa: "Chemistry of Unique Chiral Olefins. 1.Synthesis, Enantioresolution, Circular Dichroism, and Theoretical Determination of the Absolute Stereochemistry of trans-and cis-1,1', 2,2', 3,3', 4,4'-Octahydro-4,4'-biphenanthrylidenes" J.Am.Chem.Soc.119. 7241-7248 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, A.Saito, N.Koumura, D.C.Roe, W.F.Jager, R.W.J.Zijlstra, B.de Lange, and B.L.Feringa: "Chemistry of Unique Chiral Olefins. 2.Unexpected Thermal Racemization of cis-1,1', 2,2', 3,3', 4,4'-Octahydro-4,4'-biphenanthrylidenes" J.Am.Chem.Soc.119. 7249-7255 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, N.Koumura, and B.L.Feringa: "Chemistry of Unique Chiral Olefins. 3.Synthesis and Absolute Stereochemistry of trans-and cis-1,1', 2,2', 3,3', 4,4'-Octahydro-3,3'-dimethyl-4,4'-biphenanthrylidenes" J.Am.Chem.Soc.119. 7256-7264 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, H.-y.Li, T.Nehira, and M.Hagiwara: "Enantioresolution and Absolute Stereochemistry of 3,3'-Diacetyl-4,4', 6,6'-tetramethoxy-2,2'-biphenyldiol" Enantiomer. 2. 353-358 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Watanabe, T.Abe, and N.Harada: "A Convenient Synthesis of (1S,5S) -4-Alkyl-3-carbomethoxy-6,6-dimethylbicyclo [3.1.1] -hept-3-en-2-ones with Highly Optical Purity." J.Org.Chem.62. 2992-2995 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] J.-G.Dong, I.Akritopoulou-Zanze, J.Guo, N.Berova, K.Nakanishi, and N.Harada: "Theoretical Calculation of Circular Dichroic Exciton-Split Spectra in Presence of Three Interactiong 2-Naphthoate Chromophores." Enantiomer. 2. 397-409 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.-Y.Li, T.Nehira, M.Hagiwara, and N.Harada: "Total Synthesis and Absolute Stereochemistry of Natural Atropisomer of Biflavone, [CD (+) 362.0] - (-)-4', 4"', 7,7"-Tetra-O-methylcupressuflavone" J.Org.Chem.62. 7222-7227 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, K.Fujita, and M.Watanabe: "Enantioresolution and Absolute Stereochemistry of Diarylmethanols." Enantiomer. 2. 359-366 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Satake, A.Morohashi, H.Oguri, T.Oishi, M.Hirama, N.Harada, and T.Yasumoto: "The Absolute Configuration of Ciguatoxin" J.Am.Chem.Soc.119. 11325-11326 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Optical Rotation" Kagaku. 52. 48-49 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada, K.Fujita, and M.Watanabe: "Molecular Chirality by Isotopic Substitution. Synthesis, Absolute Configuration, and CD Spectra of Chiral Diphenylmethanols" Enantiomer. 3. 64-70 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Watanabe, T.Abe, Y.Fujii, and N.Harada: "Application of the CD Exciton Chirality Method to Chiral 1,2-Diamines. Use of C_<2gamma>-symmetrucal 2,3-Naphthalenedicarboximido Chromophore" Enantiomer. 3. 197-202 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Koumura and N.Harada: "X-Ray Crystallographic Determination of the Stereochemistry of a Unique Chiral Olefin, [CD(-)238.0]-(3R,3'R)-(P,P)-(Z)-(+)-1,1', 2,2', 3,3', 4,4'-Octahydro-3,3'-dimethyl-4,4'-biphenanthrylidene" Enantiomer. 3. 251-253 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Ono and N.Harada: "Synthesis, Circular Dichroism, and Absolute Stereochemistry of a Chiral Spiroaromatic, [CD(+)335.8]-(R)-15,15'-Spirobi [15H-indeno [1,2-b] naphthacene]" Enantiomer. 3. 245-250 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Goto, N.Harada, J.Crassous, and F.Diederich: "Absolute Configuration of Chiral Fullerenes and Covalent Derivatives from Their Calculated Circular Dichroism" J.Chem.Soc., Perkin. 2. 1719-1723 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Hattori, K.Sakurai, N.Koike, S.Miyano, H.Goto, F.Ishiya, and N.Harada: "Is the CD Exciton Chirality Method Applicable to Chiral 1,1'-Biphenanthryl Compounds?" J.Am.Chem.Soc.120. 9086-9087 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Koumura and N.Harada: "Photochemistry and Absolute Stereochemistry of Unique Chiral Olefins, trans- and cis-1,1', 2,2', 3,3', 4,4'-Octahydro-3,3'-dimethyl-4,4'-biphenanthrylidenes" Chem.Lett.1151-1152 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Cotton Effect" Kagaku. 54, #2. 51-53 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] R.W.J.Zijlstra, W.F.Jager, B.de Lange, P.T.van Duijnen, B.L.Feringa, H.Goto, A.Saito, N.Koumura, and N.Harada: "Chemistry of Unique Chiral Olefins. Part 4.Theoretical Studies of the Racemization Mechanism of trans-and cis-1,1', 2,2', 3,3', 4,4'-Octahydro-4,4'-biphenanthrylidenes" J.Org.Chem.(in press). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Kuwahara, K.Fujita, M.Watanabe, N.Harada, and T.Ishida: "Enantioresolution and Absolute Stereochemistry of 2-(1-Naphthyl) propane-1,2-diol and Related Compounds" Enantiomer. (in press). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "'Circular Dichroism Spectroscopy and Absolute Stereochemistry of Biologically Active Compounds' in R.Cooper and J.K.Snyder, Ed., "Advanced Bioorganic Chemistry"" Marcel Dekker, Inc., New York. (in press). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Harada: "Enantioresolution and Absolute Stereochemistry of 3,3′-Diacetyl-4,4′,6,6′-tetramethoxy-2,2′-biphenylidol." Enantiomer. 2. 353-358 (1997)

    • Related Report
      1998 Annual Research Report
  • [Publications] J.-G.Dong,N.Harada: "Theoretical Calculation of Circular Dichroic Exction-Split Spectra in Presence of Three Interactiong 2-Naphthoate Chromophores." Enantiomer. 2. 397-409 (1997)

    • Related Report
      1998 Annual Research Report
  • [Publications] N.Harada: "Enantioresolution and Absolute Stereochemistry of Diarylmethanols." Enantiomer. 2. 359-366 (1997)

    • Related Report
      1998 Annual Research Report
  • [Publications] N.Harada: "Molecular Chirality by Isotopic Substitution. Synthesis,Absolute Configuratin,and CD Spectra of Chiral Diphenylmethanols." Enantiomer. 3. 64-70 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Watanabe,N.Harada: "Application of the CD Exction Chirality Method to Chiral 1,2-Diamines.Use of C_<2v>-symmetrucal 2,3-Naphthalenedicarboximido Chromophore." Enantiomer. 3. 197-202 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] N.Koumura,N.Harada: "X-Ray Crystallographic Determination of the Stereochemistry of a Unique Chiral Olefin,[CD(-)238.0]-(3R,3′R)-(P,P)-(Z)-(+)-1,1′,2,2′,3,3′,4,4′-Octahydro-3,3′-dimethyl-4,4′-biphenanthrylidene." Enantiomer. 3. 251-253 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] H.Ono,N.Harada: "Synthesis,Circular Dichroism,and Absolute Stereochemistry of a Chiral Spiroaromatic,[CD(+)335.8]-(R)-15,15′-Spirobi[15H-indeno[1,2-b]naphthacene]." Enantiomer. 3. 245-250 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] H.Goto,N.Harada: "Absolute Configuration of Chiral Fullerenes and Covalent Derivatives from Their Calculated Circular Dichroism." J.Chem.Soc.,Perkin2. 1719-1723 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Hattori,N.Harada: "Is the CD Exction Chirality Method Applicable to Chiral 1,1'-Biphenanthryl Compounds?" J.Am.Chem.Soc.120. 9086-9087 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] N.Koumura,N.Harada: "Photochemistry and Absolute Stereochemistry of Unique Chiral Olefins,trans-and cis-1,1′,2,2′,3,3′,4,4′-Octahydro-3,3′-dimethyl-4,4′-biphenanthrylidenes." Chem.Lett.1151-1152 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 原田宣之: "コットン効果" 化学. 54,#2,. 51-53 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] R.W.J.Zijlstra,N.Harada: "Chemistry of Unique Chiral Olefins.Part4.Theoretical Studies of the Racemization Mechanism of trans-and cis-1,1′,2,2′,3,3′,4,4′-Octahydro-4,4′-biphenanthrylidenes." J.Org.Chem.in press. (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] S.Kuwahara,N.Harada: "Enantioresolution and Absolute Stereochemistry of 2-(1-Naphthyl)propane-1,2-diol and Related Compounds." Enantiomer. in press. (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] N.Harada: "‘Circular Dichroism Spectroscopy and Absolute Stereochemistry of Biologically Active Compounds,'in R.Cooper and J.K.Snyder,Ed.,“Advanced Bioorganic Chemistry"(in press)" Marcel Dekker,Inc.,New York, (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Sugioka, N.Harada,: "The CD Exciton Chirality Method and Benzoylation of Sterically Hindered α-Glycol by Trans-Esterification : Forskolin Case." Enantiomer. 2. 117-121 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] N.Harada: "Synthesis,Circular Dichroism,and Absolute Stereoshemistry of 1,1′: 4′,1″-Ternaphthalene Compounds." Chirality. 9. 623-625 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] N.Harada: "Absolute Configuration and Conformation of 1,1′: 4′,1″-Ternaphthalene Compounds as Determined by X-Ray Crystallography." Enantiomer. 2. 123-126 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] N.Harada: "Chiral Dichlorophthalic Acid Amide,an Improved Chiral Auxiliary Useful for Enantioresolution and X-Ray Crystallographic Determination of Absolute Sterochemistry." Enantiomer. 2. 303-309 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 原田宣之: "旋光度" 化学. 52. 48-49 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] H.Nemoto, N.Harada: "Lipase-Catalyzed Kinetic Resolution of Cyclobutylmethanols and Determination of Absolute Stereochemistry by X-Ray Analysis." Enantiomer. 2. 127-131 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] H.-y.Li, N.Harada: "Isolation and NMR Studies of Di-D-fructose Anhydride III from Lycoris radiata Herbert by Supercritical Extraction." Carbohydrate Research. 299. 301-305 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] N.Harada: "HMR^<13>C Satellite Signals Useful for the First-Order Analysis of Complex Spin Systems." Enantiomer. 2(in press). (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] H.Oguri, N.Harada: "Synthetic Study of Ciguatoxin. Absolute Configuration of the C2 Hydroxy Group." Tetrahedron. 53. 3057-3072 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] N.Harada: "Chemisty of Unique Chiral Olefins.1.Synthesis,Enantioresolution,Circular Dichroism,and Theoretical Determination of the Absolute Stereochemistry of trans-and cis-1,1′,2,2′,3,3′,4,4′-Octahydro-4,4′-biphenanthrylidenes." J.Am.Chem.Soc.119. 7241-7248 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] N.Harada: "Chemistry of Unique Chiral Olefins.2.Unexpected Thermal Racemization of cis-1,1′,2,2′,3,3′,4,4′-Octahydro-4,4′-biphenanthrylidenes." J.Am.Chem.Soc.119. 7249-7255 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] N.Harada: "Chemistry of Unique Chiral Olefins.3.Synthesis and Absolute Stereochemistry of trans-and cis-1,1′,2,2′,3,3′,4,4′-Octahydro-3,3′-dimethyl-4,4′-biphenanthrylidenes." J.Am.Chem.Soc.119. 7256-7264 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Kuroda, N.Harada: "Novel Cholestane Glycosides from the Bulbs of Ornithogalum saundersiae and Their Cytostatic Activity on Leukemin HL-60 and MOLT-4 Cells." Tetrahedron. 53. 11549-11562 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] N.Harada: "Enantioresolution and Absolute Stereochemistry of 3,3′-Diacetyl-4,4′,6,6′-tetramethoxy-2,2′-biphenyldiol." Enantiomer. 2(in press). (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] T.-S.Kam, N.Harada: "Tenuisines A-C and Tenuiphylline,Novel Bisindoles from Kopsia Tenuis." Tetrahedron. 53. 12661-12670 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Watanabe, N.Harada: "A Convenient Synthesis of(1S,5S)-4-Alkyl-3-carbomethoxy-6,6-dimethylbicyclo[3.1.1]-hept-3-en-2-ones with Highly Optical Purity." J.Org.Chem.62. 2992-2995 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] J.-G.Dong, N.Harada: "Theoretical Calculation of Circular Dichroic Exciton-Split Spectra in Presence of Three Interactiong 2-Naphthoate Chromophores." Enantiomer. 2(in press). (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] H.-Y.Li, N.Harada: "Total Synthesis and Absolute Stereochemistry of Natural Atropisomer of Biflavone,[CD(+)362.0]-(-)-4,4′″,7,7″-Tetra-O-methylcupressuflavone." J.Org.Chem.62. 7222-7227 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] N.Harada: "Enantioresolution and Absolute Stereochemistry of Diarylmethanols." Enantiomer. 2(in press). (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] N.Harada: "Molecular Chirality by Isotopic Substitution.Synthesis,Absolute Configuration,and CD Spectra of Chiral Diphenylmethanols." Enantiomer. 2(in press). (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Satake, N.Harada: "The Absolute Configuration of Ciguatoxin." J.Am.Chem.Soc.119. 11325-11326 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] N. Harada(M. Watanabe): "An Unexpected Selective Formation of a Lactone in the Ozonolysis of a Santonin Derivative : Neighboring Participation of a Methoxycarbonyl Group." Journal of Organic Chemistry. 60. 7372-7374 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] N. Harada: "Chiral Phthalic Acid Amide, a Chiral Auxiliary Useful for Enantiomer Resolution and X-Ray Crystallographic Determination of the Absolute Streochemistry of Alcohols." Enantiomer. 1. 35-39 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] N. Harada(Y. Mimaki): "A New Furostanol Saponin with Six Sugars from the Bulds of Allium sphaerosephalon Structural Elucidation by Modern NMR Techniques." Chemistry Letters. 431-432 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] N. Harada: "A CD Method for Determination of the Absolute Stereochemistry of Acyclic Glycols. 2. Application of the CD Exciton Chirality Method to Acyclic 1, 2-Dibenzoates Systems." Enantiomer. 1. 119-138 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] N. Harada: "Absolute Stereochemistry of [6. 6] Vespirence Family Compounds as Determined by the X-Ray Crystallography." Enantiomer. 1. 115-118 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] N. Harada: "The Recent Advances in the Spectroscopy of Circular Dichroism (CD) and Its Application for Chiral Organic Compounds." Zhurnal Organicheskoi Khimii (Russia). 32. 167-179 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] N. Harada: "CD Data Instead of [α]_D Values." Enantiomer. 1. 81-82 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 原田宣之: "日本分析化学会編「機器分析ガイドブック」第2章5節″円二色性と旋光性″" 丸善, 16 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 原田宣之: "「機器分析のてびき(2)-天然・生体有機化合物の分離分析法」第8章″旋光性と円二色性(CD)スペクトル″" 化学同人, 15 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] N.Harada: "Circular Dichroism Power of Chiral Bridged Aromatic Compounds 7,8,15,16-Tetrahydro-7,15-methanocycloocta-[1,2-a:5,6-a']dinaphthalene Derivatives." Recueil des Travaux Chimiques des Pays-Bas. 114. 157-162 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] N.Harada(H.Hagiwara): "Double Michael Reaction of Wieland-Miescher Ketone." Tetrahedron. 51. 9891-9898 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] N.Harada: "Synthesis and Absolute Stereochemistry of (+)-Adociaquinones A and B." Tetrahedron:Asymmetry. 6. 375-376 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] N.Harada(T.Hattori): "1,12-Dioxa[12](1,4)naphthalenophane-14-carboxylic Acid:Practical Synthesis,Resolution and Absolute Configuration of the Enantiomers." Tetrahedron:Asymmetry. 6. 1043-1046 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] N.Harada(F.Toda): "Enantiomer Resolution by Crystallization with Chiral Hosts:Application to Monoterpenes,Verbenone and Apoverbenone." Tetrahedron:Asymmetry. 6. 1495-1498 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] N.Harada: "Chiral Phthalic Acid Amide,a Chiral Auxiliary Useful for Enantiomer Resolution and X-Ray Crystallographic Determination of the Absolute Stereochemistry of Alcohols." Enantiomer. 1(in press). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] N.Harada: "Studies in Natural Products Chemistry Vol.17" Elsevier Science Publishers,Amsterdam, 40 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 原田宣之: "日本分析化学会編「機器分析ガイドブック」円二色性と旋光性" 丸善(印刷中), (1996)

    • Related Report
      1995 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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