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2011 Fiscal Year Final Research Report

Enantioselective total synthesis of(+)-Hydroxyapparicine, potent antimalarial indole alkaloid.

Research Project

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Project/Area Number 22790017
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKitasato University

Principal Investigator

HIROSE Tomoyasu  北里大学, 大学院・感染制御科学府, 准教授 (00370156)

Project Period (FY) 2010 – 2011
Keywords有機化学
Research Abstract

Hydroxyapparicine was isolated from Tabernaemontana dichotoma in 1984.Then, the relative stereochemistry was proposed that recorded spectral data. However, C15 stereochemistry was not showed. Therefore, absolute stereochemistry of Hydroxyapparicine has never determined. Structure fearture of hydroxyapparicine is 1-azabicyclo[4.2.2] decane and C16 chiral tertiary alchol moiety connected indole 2-position. Moreover, tertiary alchol moiety is unstable under acidic conditions. It was easliy dedydration of similar compound. From synthetic standpiont, synthesis of pseudo-aminal type alkaloids need to novel method under mild conditions. Herein, we repored the stereoselective total synthsis and determination of absolute stereochemistry of 16R-hydroxy-16, 22-dihydroapparicine(Hydroxyapparicine).

  • Research Products

    (15 results)

All 2012 2011 2010 2001 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (7 results) Remarks (1 results)

  • [Journal Article] The first total synthesis and reassignment of the relativestereochemistry of 16-hydroxy-16, 22-dihydroapparicine2012

    • Author(s)
      Yoshihiko Noguchi, Tomoyasu Hirose, Yujiro Furuya, Aki Ishiyama, Kazuhiko Otoguro, Satoshi Omura, Toshiaki Sunazuka
    • Journal Title

      Tetrahedron Lett

      Volume: Vol.53 Pages: 1082-1807

    • DOI

      DOI:10.1016/j.tetlet.2012.01.110

    • Peer Reviewed
  • [Journal Article] Three-Dimentional Solution Structure of Bottromycin A_2 : A Potent Antibiotic Active against Methicillin-Resistant Staphylococcus aureus and Vancomycin-Resistant Enterococci2012

    • Author(s)
      Hiroaki Gouda, Yutaka Kobayashi, Takeshi Yamada, Tetsuya Ideguchi, Akihiro Sugawara, Tomoyasu Hirose, Satoshi Omura, Toshiaki Sunazuka, Shuichi Hirono
    • Journal Title

      Chem. Pharm. Bull

      Volume: Vol.60 Pages: 169-171

    • DOI

      DOI:10.1248/cpb.60.169

    • Peer Reviewed
  • [Journal Article] Solution-phase total synthesis of the hydrophilic natural product argifin using 3, 4, 5-tris(octadecyloxy) benzyl tag2011

    • Author(s)
      Tomoyasu Hirose, Takako Kasai, Takafumi Akimoto, Ayako Endo, Akihiro Sugawara, Kazuo Nagasawa, Kazuro Shiomi, Satoshi Omura, Toshiaki Sunazuka
    • Journal Title

      Tetrahedron

      Volume: Vol.67 Pages: 6633-6643

    • DOI

      DOI:10.1016/j.tet.2011.05.073

    • Peer Reviewed
  • [Journal Article] Novel 12-membered non-antibiotic macrolides from erythromycin A ; EM900 series as novel leads for anti-inflammatory and/or immunomodulatory agents2011

    • Author(s)
      Akihiro Sugawara, Akito Sueki, Tomoyasu Hirose, Kenichiro Nagai, Hiroaki Gouda, Shuichi Hirono, Hideaki Shima, Kiyoko S. Akagawa, Satoshi Omura, Toshiaki Sunazuka
    • Journal Title

      Bioorg. Med. Chem. Lett

      Volume: Vol.21 Pages: 3373-3376

    • DOI

      DOI:10.1016/j.bmcl.2011.04.004

    • Peer Reviewed
  • [Journal Article] Bottromycin derivatives efficient chemical modifications of the ester moiety and evaluation of anti-MRSA and anti-VRE activities2010

    • Author(s)
      Yutaka Kobayashi, Maki Ichioka, Tomoyasu Hirose, Kenichiro Nagai, Atsuko Matsumoto, Hidehiro Matsui, Hideaki Hanaki, Rokuro Masuma, Yoko Takahashi, Satoshi Omura and Toshiaki Sunazuka
    • Journal Title

      Bioorg. Med. Chem. Lett

      Volume: Vol.20 Pages: 6116-6120

    • DOI

      DOI:10.1016/j.bmcl.2010.08.037

    • Peer Reviewed
  • [Journal Article] NMR spectroscopy and computational analysis of interaction between Serratia marcescens chitinase B and a dipeptide derived from natural-product cyclopentapeptide chitinase inhibitor argifin2010

    • Author(s)
      Hiroaki Gouda, Toshiaki Sunazuka, Tomoyasu Hirose, Kanami Iguchi, Noriyuki Yamaotsu, Akihiro Sugawara, Yoshihiko Noguchi, Yoshifumi Saito, Tsuyoshi Yamamoto, Takeshi Watanabe, Kazuro Shiomi, Satoshi Omura, Shuichi Hirono
    • Journal Title

      Bioorg. Med. Chem.

      Volume: Vol.18 Pages: 5835-5844

    • DOI

      DOI:10.1016/j.bmc.2010.06.093

    • Peer Reviewed
  • [Journal Article] Recent development of two chitinase inhibitor, Argifin and Argadin, produced by soil microorganisms2010

    • Author(s)
      Tomoyasu Hirose, Toshiaki Sunazuka, Satoshi Omura
    • Journal Title

      Proc. Jpn. Acad., Ser. B

      Volume: Vol.86 Pages: 85-102

    • DOI

      DOI:10.2183/pjab.86.85

    • Peer Reviewed
  • [Presentation] ベンジル系疎水性タグを利用した親水性天然物アージフィンの液相全合成2012

    • Author(s)
      廣瀬友靖, 笠井尚子, 秋元隆史, 遠藤綾子, 菅原章公, 長澤和夫, 大村智, 砂塚敏明
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌(北海道大学)
    • Year and Date
      2012-03-31
  • [Presentation] 疎水性タグを用いたキチナーゼ阻害剤Argifinの液相全合成2011

    • Author(s)
      廣瀬友靖、笠井尚子、秋元隆史、遠藤綾子、菅原章公、長澤和夫、塩見和朗、大村智、砂塚敏明
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島(あわぎんホール)
    • Year and Date
      20111107-08
  • [Presentation] 天然物を基にした特異的かつ強力なキチナーゼ阻害剤の創製研究2011

    • Author(s)
      廣瀬友靖
    • Organizer
      第55回日本薬学会関東支部大会
    • Place of Presentation
      習志野(東邦大学習志野キャンパス)
    • Year and Date
      2011-10-08
  • [Presentation] In Situクリックケミストリーを利用した生物活性天然物からの創薬研究2011

    • Author(s)
      廣瀬友靖
    • Organizer
      第3回全国利用・共同研究「酵素学拠点」シンポジウム~酵素学から始まる新たな創薬研究~
    • Place of Presentation
      徳島(徳島大学長井記念ホール)
    • Year and Date
      2011-10-03
  • [Presentation] Type III分泌機構阻害活性を有するGuadinomine類の不斉全合成と絶対立体構造決定2011

    • Author(s)
      廣瀬友靖、土屋智史、森龍真、田中利知、小嶋康裕、岩月正人、高橋洋子、大村智、砂塚敏明
    • Organizer
      第4回有機触媒シンポジウム
    • Place of Presentation
      東京(東京理科大学神楽坂キャンパス)
    • Year and Date
      2011-09-17
  • [Presentation] Argifinの全合成と高活性キチナーゼ阻害剤の創製研究2010

    • Author(s)
      廣瀬友靖
    • Organizer
      第3回日本薬学会関東支部若手シンポジウム
    • Place of Presentation
      東京薬科大学
    • Year and Date
      2010-10-02
  • [Presentation] Chitinase inhibitors : Extraction of the active framework from natural argifin and use of in situ click chemistry2001

    • Author(s)
      Tomoyasu Hirose, Akihiro Sugawara, Ayako Endo, Tsuyoshi Yamamoto, Kzuro Shiomi, Takeshi Watanabe, K. Barry Sharpless, Satoshi Omura, Toshiaki Sunazuka
    • Organizer
      242nd American Chemical Society National Meeting
    • Place of Presentation
      Denver, Colorado, USA
    • Year and Date
      20010828-0901
  • [Remarks]

    • URL

      http://seibutuyuuki.sakura.ne.jp/index.html

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Published: 2013-07-31  

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