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2002 Fiscal Year Final Research Report Summary

New Development of One-electron Transfer Reaction - Application to the Total Synthesis of Biologically Active Natural Products -

Research Project

Project/Area Number 13640530
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionShizuoka University

Principal Investigator

YODA Hidemi  Shizuoka University, Engineering, Associate Professor, 工学部, 助教授 (20201072)

Project Period (FY) 2001 – 2002
KeywordsSamarium / radical / imide / lactam / reductive coupling / alkaloid / indolizidine / natural product
Research Abstract

Structurally complex alkaloidal sugar mimics with a nitrogen in the ring have been isolated from plants and microorganisms and inhibit various glycosidases in a reversible and competitive manner. Since such glycosidase inhibitors proved to have the potential to produce antiviral, insect antifeedant, antidiabetic, and anticancer effects as well as immune modulatory properties, they have held considerable interest in the context of the synthesis of nitrogen-containing natural products.
Towards the carbonyl group of imides, on the other hand, two reactions, i.e., an intramolecular Barbier-type reaction of some N-iodoalkyl cyclic imides and a coupling reaction of acyclic imides such as N-acyllactams with carbonyl compounds are known. In this connection we have also recently reported the first pinacolic cross-coupling reaction between phthalimides and carbonyl compounds and its application to the complete stereoselective deoxygenation. However, the lack of studies concerning the reactivity of samarium (II) compounds towards simple amides is surprising except in some special cases. This should be attributed to their low reactivity.
Herein we described the first nitrogen-carbon (hetero) coupling reaction between lactams and aldehydes mediated by SmI_2 to provide N-α-hydroxyalkylated lactams and its application to the short synthesis of biologically active indolizidine alkaloids, (-)-δ-coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine in addition to the formal synthesis of an isoindolobenzazepine alkaloid, chilenine.

  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] Hidemi Yoda: "Asymmetric Syntheses of Trisubstituted Tetrahydrofuran Lignans, Sesaminone and 4-Epidihydrosesamin"Synlett. 400-402 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hidemi Yoda: "SmI2-mediate Hetero-coupling Reaction of Lactams with Aldehydes ; Synthesis of Indolizidine Alkaloids, (-)-δ-Coniceine, (+)-5-Epiindolizidine 167B and (+)-Lentiginosine"Tetrahedron Letters. 42. 2509-2512 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hidemi Yoda: "Asymmetric Synthesis of a New Marine Epoxy Lipid, (6S,7S,9S,10S)-6,9-Epoxynonadec-18-ene-7,1O-diol"Tetrahedron : Asymmetry. 12. 1403-1406 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hidemi Yoda: "SmI2-promoted Tandem Desulfurization and Reductive Coupling Reactions of Aromatic Lactams with Carbonyl Compounds"Tetrahedron Letters. 42. 9225-9228 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hidemi Yoda: "First Practical Asymmetric Synthesis of a New Tetrasubstituted Tetrahydrofuran, (-)-Goniothalesdiol"Synlett. 1532-1534 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hidemi Yoda: "A Novel Synthetic Approach to Isoindolobenzazepine Alkaloid, Chilenine, Employing SmI2-mediated Pinacolic Coupling Reaction"Tetrahedron Letters. 43. 4667-4669 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H. Yoda, K. Kumura and K. Takabe: "Asymmetric Syntheses of Trisubstituted Tetrahydrofuran Lignans, Sesaminone and 4-Epidihydrosesamin"Synlett.. 400-402 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Yoda, H. Katoh, Y. Ujihara and K. Takabe: "SmI_2-mediated Hetero-coupling Reaction of Lactams with Aldehydes ; Synthesis of Indolizidine Alkaloids, (-)-δ-Coniceine, (+)-5-Epiindolizidine 167B and (+)-Lentiginosine"Tetrahedron Letters. 42. 2509-2512 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Yoda, K. Maruyama and K.Takabe: "Asymmetric Synthesis of a New Marine Epoxy Lipid (6S, 7S, 9S, 10S)-6, 9-Epoxinonadec-18-ene-7, 10-diol"Tetrahedron : Asymmetry. 1403-1406 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Yoda, Y. Ujihara and K. Takabe: "SmI2-promoted Tandem Desulfurization and Reductive Coupling Reactions of Aromatic Lactams with Carbonyl Compounds"Tetrahedron Letters. 42. 9225-9228 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Yoda, Y. Nakaseko and K. Takabe: "First Practical Asymmetric Synthesis of a New Tetrasubstituted Tetrahydrofuran, (-)-Goniothalesdiol"Synlett. 1532-1534 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Yoda, A. Nakahama, T. Koketsu and K. Takabe: "A Novel Synthetic Approach to Isoindolobenzazepine Alkaloid, Chilenine, Employing SmI2-mediated Pinacolic Coupling Reaction"Tetrahedron Letters. 43. 4667-4669 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Yoda: "Recent Advances in the Synthesis of Naturally Occurring Polyhydroxylated Alkaloids"Current Organic Chemistry. 6. 223-243 (2002)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2004-04-14  

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