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Consice total synthesis of Mangromicins utilizing cascade reactions and development of new medicine for tropical disease

Research Project

Project/Area Number 15K18836
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionKitasato University

Principal Investigator

Yamada Takeshi  北里大学, 感染制御科学府, 特任助教 (00608367)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2015: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords全合成 / 抗トリパノソーマ / マングロマイシン / ディークマン反応 / βラクトン / カスケード反応 / アフリカ睡眠病 / 多置換テトラヒドロフラン / ディークマン縮合 / 多置換テトラヒドロフラン環 / 大環状炭素環
Outline of Final Research Achievements

An enantioselective total synthesis of (+)-Mangromicin A has been accomplished. Naturally occurring mangromicins are novel anti-trypanosomal compounds, which have been discovered by our group. The tetrahydrofuran ring of mangromicin A, possessing a tetra-substituted carbon center, was constructed by Mukaiyama-type vinylogous alkylation via a cyclic oxocarbenium intermediate derived from γ-hydroxy ketone, with ideal stereoselectivity, and the 4-hydoxy-dihydropyrone scaffold was generated via Dieckmann cyclization at a late stage of the total synthesis. The reliable asymmetric synthesis of (+)-mangromicin A has revealed the absolute configuration of the naturally occurring mangromicin A.

Report

(3 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • Research Products

    (25 results)

All 2017 2016 2015 Other

All Journal Article (7 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 7 results,  Open Access: 3 results,  Acknowledgement Compliant: 1 results) Presentation (16 results) (of which Int'l Joint Research: 2 results,  Invited: 3 results) Remarks (2 results)

  • [Journal Article] Total Synthesis and Determination of the Absolute Configuration of Naturally Occurring Mangromicin A, with Potent Antitrypanosomal Activity2017

    • Author(s)
      Hirokazu Takada, Takeshi Yamada, Tomoyasu Hirose, Takuma Ishihara, Takuji Nakashima, Yoko Takahashi, Satoshi Omura, Toshiaki Sunazuka
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 1 Pages: 230-233

    • DOI

      10.1021/acs.orglett.6b03512

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Ivermectin efficacy against Biomphalaria, intermediate host snail vectors of Schistosomiasis2017

    • Author(s)
      Naftale Katz, Neusa Araujo, Paulo Marcos Zech Coelho, Carlos Medicis Morel, Ana Rosa Linde-Arias, Takeshi Yamada, Yuki Horimatsu, Koh Suzuki, Toshiaki Sunazuka, Satoshi Omura
    • Journal Title

      Journal of Antibiotics

      Volume: 70 Issue: 5 Pages: 680-684

    • DOI

      10.1038/ja.2017.31

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Organocatalytic Site-Selective Acylation of Avermectin B2a, a Unique Endectocidal Drug2016

    • Author(s)
      Takeshi Yamada, Koh Suzuki, Tomoyasu Hirose, Takumi Furuta, Yoshihiro Ueda, Takeo Kawabata, Satoshi Omura, Toshiaki Sunazuka
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 54 Pages: 856-864

    • NAID

      130005160046

    • Related Report
      2016 Annual Research Report 2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Organocatalytic Site-Selective Acylation of 10-Deacetylbaccatin III2016

    • Author(s)
      Yanagi Masanori, Ryo Ninomiya, Yoshihiro Ueda, Takumi Furuta, Takeshi Yamada, Toshiaki Sunazuka, Takeo Kawabata
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 7 Pages: 907-912

    • DOI

      10.1248/cpb.c16-00037

    • NAID

      130005160042

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Annual Research Report 2015 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Asymmetric Total Synthesis of Indole Alkaloids Containing an Indoline Spiroaminal Framework2015

    • Author(s)
      Takeshi Yamada, Tetsuya Ideguchi-Matsushita, Tomoyasu Hirose, Tatsuya Shirahata, Rei Hokari, Aki Ishiyama, Masato Iwatsuki, Akihiro Sugawara, Yoshinori Kobayashi, Kazuhiko Otoguro, Satoshi Omura, Toshiaki Sunazuka
    • Journal Title

      Chemistry - A European Journal

      Volume: 21 Issue: 33 Pages: 11855-11864

    • DOI

      10.1002/chem.201501150

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Jietacins with potent nematocidal activity; efficient isolation of novel analogues and divergent total synthesis of jietacin A, B, C, and D2015

    • Author(s)
      4) Akihiro Sugawara, Masahiko Kubo, Takuji Nakashima, Tomoyasu Hirose, Noriaki Tsunoda, Kyoichi Yahagi, Yukihiro Asami, Takeshi Yamada, Kazuro Shiomi, Yoko Takahashi, Satoshi Omura, Toshiaki Sunazuka
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 14 Pages: 2149-2157

    • DOI

      10.1016/j.tet.2015.02.038

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Organocatalytic α-Addition of Isocyanides to Aldehydes2015

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

      Eur. J. Org. Chem.

      Volume: 2015 Issue: 2 Pages: 296-301

    • DOI

      10.1002/ejoc.201403313

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Presentation] 抗トリパノソーマ活性を有するMangromicin Aの全合成と絶対立体構造の決定2017

    • Author(s)
      高田拓和、山田健、廣瀬友靖、石原拓真、中島琢自、高橋洋子、大村智、砂塚敏明
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学川内北キャンパス(宮城県仙台市)
    • Year and Date
      2017-03-27
    • Related Report
      2016 Annual Research Report
  • [Presentation] 顧みられない熱帯病、トリパノソーマ症に有効なマングロマイシン類の全合成研究2016

    • Author(s)
      高田拓和、山田健、廣瀬友靖、石原拓真、中島琢自、高橋洋子、大村智、砂塚敏明
    • Organizer
      第110回有機合成シンポジウム2016年【秋】
    • Place of Presentation
      早稲田大学国際会議場(東京都新宿区)
    • Year and Date
      2016-11-11
    • Related Report
      2016 Annual Research Report
  • [Presentation] 有機分子触媒を用いたアルデヒドとイソシアニドのα-付加反応2016

    • Author(s)
      山田健、廣瀬友靖、大村智、砂塚敏明
    • Organizer
      第110回有機合成シンポジウム2016年【秋】
    • Place of Presentation
      早稲田大学国際会議場(東京都新宿区)
    • Year and Date
      2016-11-11
    • Related Report
      2016 Annual Research Report
  • [Presentation] 有機分子触媒による10-Deacetylbaccatin IIIの位置選択的アシル化2016

    • Author(s)
      柳正致, 二宮良, 上田善弘, 山田健, 砂塚敏明, 川端猛夫
    • Organizer
      第66回日本薬学会近畿支部総会・大会
    • Place of Presentation
      大阪薬科大学(大阪府高槻市)
    • Year and Date
      2016-10-15
    • Related Report
      2016 Annual Research Report
  • [Presentation] 特徴的な構造を有する微生物由来生物活性天然物の全合成2016

    • Author(s)
      山田健
    • Organizer
      第4回慶応有機化学若手シンポジウム
    • Place of Presentation
      慶應義塾大学矢上キャンパス(神奈川県横浜市)
    • Year and Date
      2016-05-07
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 特徴的な構造を有する微生物由来生物活性天然物の全合成2016

    • Author(s)
      山田健
    • Organizer
      第4回慶応有機化学若手シンポジウム
    • Place of Presentation
      慶応大学矢上キャンパス(神奈川県横浜市)
    • Year and Date
      2016-05-07
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] 10-Deacetylbaccatin IIIの触媒的位置選択的アシル化2016

    • Author(s)
      柳正致, 二宮良, 上田善弘, 山田健, 砂塚敏明, 川端猛夫
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-29
    • Related Report
      2015 Research-status Report
  • [Presentation] 特異な三環性骨格を有するマングロマイシンの全合成研究2016

    • Author(s)
      高田拓和, 山田健, 廣瀬友靖, 中島琢自, 高橋洋子, 大村智, 砂塚敏明
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-29
    • Related Report
      2015 Research-status Report
  • [Presentation] 有機分子触媒を用いた有用天然物Avermectin B2aの位置選択的アシル化2016

    • Author(s)
      山田健, 鈴木航, 廣瀬友靖, 穂坂美聡, 古田巧, 上田善弘, 川端猛夫, 大村智, 砂塚敏明
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-28
    • Related Report
      2015 Research-status Report
  • [Presentation] Development of organocatalyst and its application toward the synthesis of bioactive natural product2015

    • Author(s)
      Takeshi Yamada, Tomoyasu Hirose, Satoshi Omura, Toshiaki Sunazuka
    • Organizer
      The 2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015)
    • Place of Presentation
      Hawaii, USA
    • Year and Date
      2015-12-17
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Total Synthesis of Indole Alkaloids Containing an Indoline Spiroaminal Framework2015

    • Author(s)
      Takeshi Yamada, Tetsuya Ideguchi, Tomoyasu Hirose, Tatsuya Shirahata, Rei Hokari, Aki Ishiyama, Masato Iwatsuki, Akihiro Sugawara, Yoshinori Kobayashi, Kazuhiko Otoguro, Satoshi Omura, Toshiaki Sunazuka
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)
    • Place of Presentation
      リーガロイヤルホテル京都(京都府京都市)
    • Year and Date
      2015-11-10
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 特異な三環性骨格を有するマングロマイシン類の全合成研究2015

    • Author(s)
      高田拓和, 山田健, 廣瀬友靖, 中島琢自, 高橋洋子, 大村智, 砂塚敏明
    • Organizer
      AKPS集会 第9回北里化学シンポジウム
    • Place of Presentation
      北里大学白金キャンパス(東京都港区)
    • Year and Date
      2015-09-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 抗寄生虫薬Ivermectinのスピロケタール部改変アナログの合成と抗線虫活性2015

    • Author(s)
      鈴木航, 山田健, 堀松優樹, 廣瀬友靖, 大村智, 砂塚敏明
    • Organizer
      AKPS集会 第9回北里化学シンポジウム
    • Place of Presentation
      北里大学白金キャンパス(東京都港区)
    • Year and Date
      2015-09-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 抗MRSA, VRE活性を有するBottromycin A2の全合成とチアゾール改変アナログの合成2015

    • Author(s)
      八木田美有, 山田健, 廣瀬友靖, 大村智, 砂塚敏明
    • Organizer
      AKPS集会 第9回北里化学シンポジウム
    • Place of Presentation
      北里大学白金キャンパス(東京都港区)
    • Year and Date
      2015-09-26
    • Related Report
      2015 Research-status Report
  • [Presentation] インドリンスピロアミナール骨格を有する天然物の全合成と生物活性2015

    • Author(s)
      山田健, 井手口哲也, 廣瀬友靖, 白畑辰弥, 穂刈怜, 石山亜紀, 岩月正人, 菅原章公, 小林義典, 乙黒一彦, 大村智, 砂塚敏明
    • Organizer
      AKPS集会 第9回北里化学シンポジウム
    • Place of Presentation
      北里大学白金キャンパス(東京都港区)
    • Year and Date
      2015-09-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 抗嫌気性菌活性を有するルミナミシンの全合成研究2015

    • Author(s)
      君嶋葵, 高田拓和, 菅原章公, 安藤博康, 諸留圭介, 松丸尊紀, 山田健, 廣瀬友靖, 大村智, 砂塚敏明
    • Organizer
      第57回天然有機化合物討論会
    • Place of Presentation
      神奈川県民ホール(神奈川県横浜市)
    • Year and Date
      2015-09-11
    • Related Report
      2015 Research-status Report
  • [Remarks]

    • URL

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

    • Related Report
      2016 Annual Research Report
  • [Remarks]

    • URL

      http://seibutuyuuki.sakura.ne.jp

    • Related Report
      2015 Research-status Report

URL: 

Published: 2015-04-16   Modified: 2018-03-22  

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