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Synthetic studies on portimine, a potent and selective inducer of apoptosis

Research Project

Project/Area Number 15K07861
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionNagasaki University

Principal Investigator

ISHIHARA Jun  長崎大学, 医歯薬学総合研究科(薬学系), 教授 (80250413)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords有機合成化学 / 海産天然物 / 全合成 / 環状アセタール / ポルチミン / 合成化学 / 天然物化学 / アポトーシス / 天然物合成 / ビスアルコキシシラン
Outline of Final Research Achievements

In late years, apoptosis has been revealed to play an important role for cancer and autoimmune disease. Portimine is a polycyclic marine toxin isolated from the dinoflagellate. The biological studies of this compound indicated that it has potent antitumor activity and also shows the activation of caspases indicating apoptotic activity. In this work, we studied the synthesis of portimine, which contains five-membered cyclic mine moiety and remarkable dioxabicyclo[6.2.1]undecanone embedded in macrocyclic framework. Brown's asymmetric crotylation and silyl linkage-mediated coupling afforded an acyclic key intermediate. This acyclic compound was subjected to acid to generate a core acetal.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (36 results)

All 2018 2017 2016 2015 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Acknowledgement Compliant: 6 results) Presentation (25 results) (of which Int'l Joint Research: 6 results,  Invited: 2 results) Remarks (1 results) Funded Workshop (1 results)

  • [Journal Article] Stereoselective Synthesis of the Right-hand Cores of 16-Methylated Oxazolomycins2018

    • Author(s)
      Kohei Eto, Jun Ishihara, Susumi Hatakeyama
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 7 Pages: 711-719

    • DOI

      10.1016/j.tet.2017.12.036

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Construction of Entire Diastereomeric Stereotetrads Based on an Asymmetric Morita-Baylis-Hillman Reaction2017

    • Author(s)
      Hikaru Yoshimura, Jun Ishihara, Susumi Hatakeyama
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 印刷中 Issue: 19 Pages: 2719-2729

    • DOI

      10.1002/ejoc.201700337

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Ionic Liquid-Mediated Hydrofluorination of o-Azaxylylenes Derived From 3-Bromo-oxindoles2017

    • Author(s)
      Satoshi Mizuta, Hiroki Otaki, Ayako Kitagawa , Kanami Kitamura, Yuki Morii, Jun Ishihara, Kodai Nishi, Ryo Hashimoto, Toshiya Usui, and Kenya Chiba
    • Journal Title

      Organic Letters

      Volume: 印刷中 Issue: 10 Pages: 2572-2575

    • DOI

      10.1021/acs.orglett.7b00887

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Concise Formation of Spirocyclic Compounds for Marine Phycotoxins2017

    • Author(s)
      Jun Ishihara, Shingo Tojo, Takuya Makino, Hiroshi Sekiya, Akiko Tanabe, Mitsutaka Shiraishi, Akio Murai, Susumi Hatakeyama
    • Journal Title

      Heterocycles

      Volume: 95 Issue: 1 Pages: 422-444

    • DOI

      10.3987/com-16-s(s)34

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Protecting-Group-Free Synthesis of (+)-9,10-Dihydroecklonialactone B2017

    • Author(s)
      Asmaa Said Ali Yassen, Jun Ishihara, Susumi Hatakeyama
    • Journal Title

      Heterocycles

      Volume: 94 Issue: 1 Pages: 59-63

    • DOI

      10.3987/com-16-13602

    • NAID

      40021106932

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Stereoselective Approach toward Ophiodilactones Based on an Intramolecular [2+2] Cycloaddition Reaction2015

    • Author(s)
      Takaaki Matsubara, Jun Ishihara, Susumi Hatakeyama
    • Journal Title

      Heterocycles

      Volume: 90 Issue: 1 Pages: 405-424

    • DOI

      10.3987/com-14-s(k)32

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Lewis Acid Template-Catalyzed Asymmetric Diels-Alder Reaction2015

    • Author(s)
      Jun Ishihara, Shino Nakadachi, Yuki Watanabe, Susumi Hatakeyama
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 80 Issue: 4 Pages: 2037-2041

    • DOI

      10.1021/acs.joc.5b00055

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (-)-N-Methylwelwitindolinone C Isothiocyanate Based on a Pd-Catalyzed Tandem Enolate Coupling Strategy2015

    • Author(s)
      Komine, Keita; Nomura, Yusuke; Ishihara, Jun; Hatakeyama, Susumi
    • Journal Title

      Organic Letters

      Volume: 17 (15) Issue: 15 Pages: 3918-3921

    • DOI

      10.1021/acs.orglett.5b01952

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Unified Synthesis of Tirandamycins and Streptolydigins2015

    • Author(s)
      Yoshimura, Hikaru; Takahashi, Keisuke; Ishihara, Jun; Hatakeyama, Susumi
    • Journal Title

      Chemical Communications

      Volume: (51) Issue: 95 Pages: 17004-17007

    • DOI

      10.1039/c5cc07749d

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Progress toward the Total Synthesis of Spirolide B, a Macrocyclic Marine Phycotoxin2018

    • Author(s)
      Jun Ishihara
    • Organizer
      The 18th Florida Heterocyclic and Synthetic Conference (FloHet 2018)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] ハリクロニン A の形式合成2018

    • Author(s)
      浦山 泰洋,小嶺 敬太,保坂 拓, 山下 裕貴,石原 淳,畑山 範2 畑山 範, 石原 淳
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] スピロイミナール骨格を有するアルカロイド、マリネオシン A および B の合成研究2018

    • Author(s)
      森井 優樹,菅 晃久,山元 広平,石原 淳,畑山 範
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Lewis 酸テンプレートを触媒とする不斉ヘテロ Diels-Alder 反応の開発2018

    • Author(s)
      岡 賢吾,大園 侑花,浦山 泰洋,畑山 範,石原 淳
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] マリネオシンA、Bの合成研究2017

    • Author(s)
      菅 晃久,山元 広平, 石原 淳 ,畑山 範
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学川内キャンパス(宮城県仙台市)
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] 海産毒天然物スピロリドBの合成研究2017

    • Author(s)
      碓井 風馬,黒瀬 朋浩,川口 康徳,畑山 範,石原 淳
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学川内キャンパス(宮城県仙台市)
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] Progress toward the Total Synthesis of Spirolide, a Macrocyclic Marine Phycotoxin2017

    • Author(s)
      Jun Ishihara, Fuma Usui, Tomohiro Kurose, Shino Nakadachi, Yasunori Kawaguchi, Susumi Hatakeyama
    • Organizer
      26th French-Japanese Symposium on Medicinal & Fine Chemistry
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] イソパルヒニンAの全合成研究2017

    • Author(s)
      松本 啓秀,畑山 範,石原 淳
    • Organizer
      第34回日本薬学会九州支部大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] マクロリド天然物ツガシン cmc-A の合成研究2017

    • Author(s)
      松本 萌,岩崎 瞳,富澤 慧,西丸 達也,石原 淳,Jacques Eustache,畑山 範
    • Organizer
      第34回日本薬学会九州支部大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Lewis酸テンプレートを触媒とする不斉Diels-Alder反応の開発2017

    • Author(s)
      石原 淳,仲達 偲乃,渡邊 由貴,大園 侑花,浦山 泰洋,岡 賢吾,畑山 範
    • Organizer
      第43回反応と合成の進歩シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 海産毒ギムノジミンの合成研究2017

    • Author(s)
      山中 未歩、仲達 偲乃,渡邊 由貴,畑山 範,石原 淳
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 環状アルカロイド天然物ハリクロニンAの合成研究2017

    • Author(s)
      浦山 泰洋、小嶺 敬太、保坂 拓、山下 裕貴、石原 淳、畑山 範
    • Organizer
      第59回天然有機化合物討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 光学活性(+)-910-ジヒドロエクロニアラクトンBの合成2017

    • Author(s)
      Asmaa Said Ali Yassen, 石原 淳, 畑山 範
    • Organizer
      第27回万有福岡シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] イオン性液体を媒体とした求核的フッ素化反応2017

    • Author(s)
      森井 優樹, 水田 賢志, 畑山 範, 石原 淳
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学川内キャンパス(宮城県仙台市)
    • Related Report
      2016 Research-status Report
  • [Presentation] クルチオリドの全合成研究2016

    • Author(s)
      坂井 良輔,水流 裕明,石原 淳,畑山 範
    • Organizer
      第33回日本薬学会九州支部大会
    • Place of Presentation
      鹿児島大学郡元キャンパス(鹿児島県鹿児島市)
    • Year and Date
      2016-12-03
    • Related Report
      2016 Research-status Report
  • [Presentation] 大環状アルカロイド、ポルチミンの全合成研究2016

    • Author(s)
      下岡 巧弥,石原 淳,畑山 範
    • Organizer
      第33回日本薬学会九州支部大会
    • Place of Presentation
      鹿児島大学郡元キャンパス(鹿児島県鹿児島市)
    • Year and Date
      2016-12-03
    • Related Report
      2016 Research-status Report
  • [Presentation] 抗腫瘍活性を有するイグジグオリドの全合成研究2016

    • Author(s)
      淵 駿介,石原 淳,畑山 範
    • Organizer
      第33回日本薬学会九州支部大会
    • Place of Presentation
      鹿児島大学郡元キャンパス(鹿児島県鹿児島市)
    • Year and Date
      2016-12-03
    • Related Report
      2016 Research-status Report
  • [Presentation] タンデムラジカル環化反応を基盤としたハリクロニン A の合成研究2016

    • Author(s)
      小嶺 敬太,保坂 拓,山下 裕貴,石原 淳、畑山 範
    • Organizer
      第42回反応と合成の進歩シンポジウム
    • Place of Presentation
      静岡市清水文化会館マリナート(静岡県静岡市)
    • Year and Date
      2016-11-07
    • Related Report
      2016 Research-status Report
  • [Presentation] 不斉森田-Baylis-Hillman反応を活用するポリプロピオネート構築2016

    • Author(s)
      吉村 光,石原 淳,畑山 範
    • Organizer
      第42回反応と合成の進歩シンポジウム
    • Place of Presentation
      静岡市清水文化会館マリナート(静岡県静岡市)
    • Year and Date
      2016-11-07
    • Related Report
      2016 Research-status Report
  • [Presentation] ツガシンcmc-Aの合成研究2016

    • Author(s)
      松本 萌,岩崎 瞳,富澤 慧,西丸 達也,石原 淳,Jacques Eustache,畑山 範
    • Organizer
      第58回天然有機化合物討論会
    • Place of Presentation
      東北大学川内萩ホール(宮城県仙台市)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] Lewis acid template-catalyzed asymmetric Diels-Alder reaction and its application to natural product synthesis2016

    • Author(s)
      Jun Ishihara, Shino Nakadachi, Yuki Watanabe, Susumi Hatakeyama
    • Organizer
      25th French-Japanese Symposium of Medicinal and Fine Chemistry
    • Place of Presentation
      京王プラザホテル多摩(東京都多摩市)
    • Year and Date
      2016-05-16
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] ツガシンcmc-Aの合成研究2016

    • Author(s)
      松本 萌,岩崎 瞳,富澤 慧,西丸 達也,石原 淳,Jacques Eustache,畑山 範
    • Organizer
      第26回万有福岡シンポジウム
    • Place of Presentation
      九州大学医学部百年講堂(福岡県福岡市)
    • Year and Date
      2016-04-23
    • Related Report
      2016 Research-status Report
  • [Presentation] Lewis Acid Template-catalyzed Asymmetric Diels-Alder Reaction and its Application Towards the Total Synthesis of Macrocyclic Imine Phycotoxins2015

    • Author(s)
      J. Ishihara, Y. Nakadachi, Y. Watanabe, S. Hatakeyama
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015
    • Place of Presentation
      ホノルル(米国)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Lewis Acid Template-Catalyzed Asymmetric Diels-Alder Reaction2015

    • Author(s)
      J. Ishihara, Y. Nakadachi, Y. Watanabe, S. Hatakeyama
    • 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
      2015-11-09
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Lewis Acid Template-catalyzed Asymmetric Diels-Alder Reaction and Its Application Towards the Total Synthesis of Macrocyclic Imine Phycotoxins2015

    • Author(s)
      J. Ishihara
    • Organizer
      BIT’s 6th Annual Global Congress of Catalysis-2015
    • Place of Presentation
      西安(中国)
    • Year and Date
      2015-09-24
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Remarks] 長崎大学薬学部薬品製造化学研究室

    • URL

      http://www.ph.nagasaki-u.ac.jp/lab/manufac/index-j.html

    • Related Report
      2017 Annual Research Report 2016 Research-status Report 2015 Research-status Report
  • [Funded Workshop] 26th French-Japanese Symposium on Medicinal & Fine Chemistry2017

    • Related Report
      2017 Annual Research Report

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Published: 2015-04-16   Modified: 2019-03-29  

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