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2011 Fiscal Year Final Research Report

Studies on Molecular Science of Biologically Active Natural Products Based on Chemical Synthesis

Research Project

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Project/Area Number 20310137
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Living organism molecular science
Research InstitutionOsaka City University

Principal Investigator

MORIMOTO Yoshiki  大阪市立大学, 大学院・理学研究科, 教授 (90244631)

Co-Investigator(Renkei-kenkyūsha) DOE Matsumi  大阪市立大学, 大学運営本部, 技術職員 (90433317)
Project Period (FY) 2008 – 2011
Keywords生物活性分子の設計・合成 / 化学合成
Research Abstract

To advance studies on molecular science of triterpene polyethers and alkaloids, biologically active natural products(secondary metabolites from organisms), their chemical syntheses were carried out. As a result, we have succeeded in determining the entire stereostructure of omaezakianol by the asymmetric total synthesis, developing the chemical synthesis method of isodehydrothyrsiferol, and chemically reproducing biomimetic oxacyclizations of teurilene and ekeberin D_4.In addition, an efficient synthesis of the indeno-tetrahydropyridine skeleton of houamine B has also been accomplished.

  • Research Products

    (36 results)

All 2012 2011 2010 2009 2008 Other

All Journal Article (13 results) (of which Peer Reviewed: 13 results) Presentation (20 results) Book (2 results) Remarks (1 results)

  • [Journal Article] Total Synthesis of Marine Halogen-Containing Triterpene Polyethers Using Regioselective 5-exo and 6-endo Cyclizations and the Stereochemistry2012

    • Author(s)
      Yoshiki Morimoto
    • Journal Title

      J. Synth. Org. Chem., Jpn.

      Volume: 70 Pages: 154-165

    • DOI

      DOI:10.5059/yukigoseikyokaishi.70.154

    • Peer Reviewed
  • [Journal Article] Rings D-Seco and B, D-Seco Tetranortriterpenoids from Root Bark of Entandrophragma angolense2011

    • Author(s)
      Nsiama Tienabe Kipassa, Hiroaki Okamura, Toshiyuki Hamada, Yoshiki Morimoto, Matsumi Doe, Tetsuo Iwagawa, and Munehiro Nakatani
    • Journal Title

      Phytochemistry

      Volume: 72 Pages: 1854-1858

    • URL

      http://dx.doi.org/10.1016/j.phytochem.2011.05.014

    • Peer Reviewed
  • [Journal Article] Cytotoxic Eunicellin-Type Diterpenes from the Soft Coral Liophyton viscudium2011

    • Author(s)
      Tetsuo Iwagawa, Taiki Kusatsu, Keiko Tsuha, Toshiyuki Hamada, Hiroaki Okamura, Tatsuhiko Furukawa, Shin-ichi Akiyama, Matsumi Doe, Yoshiki Morimoto, Fumihito Iwase, and Kaoru Takemura
    • Journal Title

      Heterocycles

      Volume: 83 Pages: 2149-2155

    • DOI

      DOI:10.3987/COM-11-12251

    • Peer Reviewed
  • [Journal Article] Diastereoselective Synthesis of the Indeno-Tetrahydropyridine Core Bearing a Diaryl-Substituted Stereogenic Quaternary Carbon Center of Haouamine B2011

    • Author(s)
      Takeshi Tanaka, Hiromi Inui, Hiroshi Kida, Takeshi Kodama, Takuya Okamoto, Aki Takeshima, Yoshimitsu Tachi, and Yoshiki Morimoto
    • Journal Title

      Chem. Commun.

      Volume: 47 Pages: 2949-2951

    • DOI

      DOI:10.1039/C0CC04453A

    • Peer Reviewed
  • [Journal Article] TIPSOTf-Promoted Tandem Reaction through Rearrangement of Epoxides into Aldehydes with Selective Alkyl Migration Followed by the Prins-Type Cyclization to Cyclopentanes2010

    • Author(s)
      Takeshi Kodama, Shingo Harada, Takeshi Tanaka, Yoshimitsu Tachi, and Yoshiki Morimoto
    • Journal Title

      Synlett

      Volume: 23 Pages: 458-462

    • DOI

      DOI:10.1055/s-0031-1290324

    • Peer Reviewed
  • [Journal Article] Cytotoxic Isomalabaricane Derivatives and a Monocyclic Triterpene Glycoside from the Sponge Rhabdastrella globostellata2010

    • Author(s)
      Miyabi Hirashima, Kazuomi Tsuda, Toshiyuki Hamada, Hiroaki Okamura, Tatsuhiko Furukawa, Shin-ichi Akiyama, Yusuke Tajitsu, Ryuji Ikeda, Masaharu Komatsu, Matsumi Doe, Yoshiki Morimoto, Motoo Shiro, Rob W. M. van Soest, Kaoru Takemura, and Tetsuo Iwagawa
    • Journal Title

      J. Nat. Prod.

      Volume: 73 Pages: 1512-1518

    • DOI

      DOI:10.1021/np100302a

    • Peer Reviewed
  • [Journal Article] Cytotoxic Biscembranes from the Soft Coral Sarcophyton glaucum2009

    • Author(s)
      Tetsuo Iwagawa, Kanta Hashimoto, Yukiko Yokogawa, Hiroaki Okamura, Munehiro Nakatani, Matsumi Doe, Yoshiki Morimoto, and Kaoru Takemura
    • Journal Title

      J. Nat. Prod.

      Volume: 72 Pages: 946-949

    • DOI

      DOI:10.1021/np8003485

    • Peer Reviewed
  • [Journal Article] Total Synthesis and Determination of the Absolute Configuration of(+)-Omaezakianol2009

    • Author(s)
      Yoshiki Morimoto, Tatsuya Okita, and Hitomi Kambara
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 48 Pages: 2538-2541

    • DOI

      DOI:10.1002/anie.200805857

    • Peer Reviewed
  • [Journal Article] Aplysinopsin Dimers from a Stony Coral. Tubastraea aurea2008

    • Author(s)
      Tetsuo Iwagawa, Miho Miyazaki, Yukiko Yokogawa, Hiroaki Okamura, Munehiro Nakatani, Matsumi Doe, Yoshiki Morimoto, and Kaoru Takemura
    • Journal Title

      Heterocycles

      Volume: 75 Pages: 2023-2028

    • DOI

      DOI:10.3987/COM-08-11358

    • Peer Reviewed
  • [Journal Article] Limonoids from the Stem Bark of Cedrela odorata2008

    • Author(s)
      Nsiama Tienabe Kipassa, Tetsuo Iwagawa, Hiroaki Okamura, Matsumi Doe, Yoshiki Morimoto, and Munehiro Nakatani
    • Journal Title

      Phytochemistry

      Volume: 69 Pages: 1782-1787

    • URL

      http://dx.doi.org/10.1016/j.phytochem.2007.12.015

    • Peer Reviewed
  • [Journal Article] The Role of Chemical Synthesis in Structure Elucidation of Oxasqualenoids2008

    • Author(s)
      Yoshiki Morimoto
    • Journal Title

      Org. Biomol. Chem.

      Volume: 6 Pages: 1709-1719

    • DOI

      DOI:10.1039/B801126E

    • Peer Reviewed
  • [Journal Article] Squalene-Derived Triterpene Polyethers from the Red Alga Laurencia omaezakiana2008

    • Author(s)
      Yoshihide Matsuo, Minoru Suzuki, Michio Masuda, Toshiyuki Iwai, and Yoshiki Morimoto
    • Journal Title

      Helv. Chim. Acta

      Volume: 91 Pages: 1261-1266

    • DOI

      DOI:10.1002/hlca.200890137

    • Peer Reviewed
  • [Journal Article] Three Mexicanolides from the Root Bark of Entandrophragma angolense2008

    • Author(s)
      Nsiama Tienabe Kipassa, Hiroaki Okamura, Matsumi Doe, Yoshiki Morimoto, Tetsuo Iwagawa, and Munehiro Nakatani
    • Journal Title

      Heterocycles

      Volume: 75 Pages: 157-164

    • DOI

      DOI:10.3987/COM-07-11085

    • Peer Reviewed
  • [Presentation] Synthetic Studies on Isodehydrothyrsiferol2011

    • Author(s)
      Yoshiki Morimoto
    • Organizer
      The 16th Osaka City University International Symposium on Dynamic Molecular Devices
    • Place of Presentation
      Osaka City University(Osaka)
    • Year and Date
      2011-11-09
  • [Presentation] エポキシドの加水分解反応を引き金とする仮想生合成様オキサ環化反応に基づくオキササイクリックテルペノイドの全合成2011

    • Author(s)
      森本善樹
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪国際交流センター(大阪市)
    • Year and Date
      2011-09-29
  • [Presentation] トリテルペンポリエーテルの生合成鍵反応の研究2011

    • Author(s)
      森本善樹
    • Organizer
      2011旭硝子財団助成研究発表会
    • Place of Presentation
      ホテルグランドビル市ヶ谷(東京都)
    • Year and Date
      2011-07-26
  • [Presentation] 仮想生合成経路を模倣したオキササイクリックテルペノイドの合成研究2011

    • Author(s)
      森本善樹
    • Organizer
      第46回天然物化学談話会
    • Place of Presentation
      熱川ハイツ(静岡県)
    • Year and Date
      2011-07-07
  • [Presentation] ハウアミンBの合成研究2011

    • Author(s)
      森本善樹
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(横浜市)
    • Year and Date
      2011-03-29
  • [Presentation] 生合成前駆体モデルポリエポキシドの環化反応様式2011

    • Author(s)
      森本善樹
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(横浜市)
    • Year and Date
      2011-03-29
  • [Presentation] Synthetic Studies on Haouamines2010

    • Author(s)
      Yoshiki Morimoto
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu(USA)
    • Year and Date
      2010-12-19
  • [Presentation] 生合成様環化反応による(+)-Neroplofurol及び(+)-Ekeberin D_4の全合成2010

    • Author(s)
      森本善樹
    • Organizer
      第30回有機合成若手セミナー
    • Place of Presentation
      大阪府立大学(堺市)
    • Year and Date
      2010-11-10
  • [Presentation] 天然物ハウアミン類が有する3-アザ-[7]-パラシクロファン骨格の合成研究2010

    • Author(s)
      森本善樹
    • Organizer
      第30回有機合成若手セミナー
    • Place of Presentation
      大阪府立大学(堺市)
    • Year and Date
      2010-11-10
  • [Presentation] 生合成前駆体モデルテトラエポキシドの環化反応生成物2010

    • Author(s)
      森本善樹
    • Organizer
      第30回有機合成若手セミナー
    • Place of Presentation
      大阪府立大学(堺市)
    • Year and Date
      2010-11-10
  • [Presentation] ハウアミンBの合成研究2010

    • Author(s)
      森本善樹
    • Organizer
      第52回天然有機化合物討論会
    • Place of Presentation
      グランシップ(静岡市)
    • Year and Date
      2010-09-29
  • [Presentation] 生合成を模倣したエケベリンD_4及びラスパシオニンの合成研究2010

    • Author(s)
      森本善樹
    • Organizer
      第45回天然物化学談話会
    • Place of Presentation
      ホテル明山荘(愛知県)
    • Year and Date
      2010-07-06
  • [Presentation] 生合成前駆体モデルテトラエポキシドの環化反応生成物2010

    • Author(s)
      森本善樹
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学(東大阪市)
    • Year and Date
      2010-03-28
  • [Presentation] (+)-エケベリンD_4の全合成2010

    • Author(s)
      森本善樹
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学(東大阪市)
    • Year and Date
      2010-03-28
  • [Presentation] Isodehydrothyrsiferolの合成研究2009

    • Author(s)
      森本善樹
    • Organizer
      第29回有機合成若手セミナー
    • Place of Presentation
      甲南大学ポートアイランドキャンパス(神戸市)
    • Year and Date
      2009-11-24
  • [Presentation] スクアレン由来トリテルペンポリエーテルの全合成と立体化学2009

    • Author(s)
      森本善樹
    • Organizer
      住友化学講演会(招待講演)
    • Place of Presentation
      住友化学株式会社農業化学品研究所(宝塚市)
    • Year and Date
      2009-09-11
  • [Presentation] NMR+有機合成→全立体構造解明2009

    • Author(s)
      森本善樹
    • Organizer
      有機合成夏期セミナー「明日の有機合成化学」
    • Place of Presentation
      大阪科学技術センター(大阪市)
    • Year and Date
      2009-09-03
  • [Presentation] Isodehydrothyrsiferolの合成研究2009

    • Author(s)
      森本善樹
    • Organizer
      第36回有機反応懇談会
    • Place of Presentation
      関西学院大学(三田市)
    • Year and Date
      2009-08-03
  • [Presentation] 生合成仮説による海洋産トリテルペンポリエーテルオマエザキアノールの全合成2008

    • Author(s)
      森本善樹
    • Organizer
      第28回有機合成若手セミナー
    • Place of Presentation
      大阪大学(吹田市)
    • Year and Date
      2008-11-12
  • [Presentation] 生合成仮説による海洋産トリテルペンポリエーテルオマエザキアノールの全合成2008

    • Author(s)
      森本善樹
    • Organizer
      第35回有機反応懇談会
    • Place of Presentation
      大阪市立大学(大阪市)
    • Year and Date
      2008-08-01
  • [Book] 天然物合成で活躍した反応-実験のコツとポイント2011

    • Author(s)
      森本善樹, 他
    • Total Pages
      136-137, 166-167
    • Publisher
      化学同人
  • [Book] 天然物の全合成2000-2008(日本)2009

    • Author(s)
      森本善樹, 他
    • Total Pages
      12-13, 218-219
    • Publisher
      化学同人
  • [Remarks]

    • URL

      http://www.sci.osaka-cu.ac.jp/chem/org2/org2j.html

URL: 

Published: 2013-07-31  

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