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Application of regioselective addition reaction of organoboronic acids to allenes using platinum and palladium catalysts

Research Project

Project/Area Number 21790016
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionThe University of Tokushima

Principal Investigator

YOSHIDA Masahiro  The University of Tokushima, 大学院・ヘルスバイオサイエンス研究部, 准教授 (10344681)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2010: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2009: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywords有機化学 / パラジウム / 白金 / アレン / ボロン酸 / 全合成 / 立体選択的反応 / 不斉合成 / クライゼン転移
Research Abstract

For the evolution of the palladium- and platinum-catalyzed addition of arylboronic acids to allenes, we examined the application to the total syntheses of natural products, and the development of cascade cyclization reaction. As the result, we have achieved the total syntheses of enokipodin A and aplysin. As the cascade cyclization, it has been found that platinum-catalyzed cascade addition-cyclization of allenes with arylboronic acids.

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (42 results)

All 2011 2010 2009 Other

All Journal Article (18 results) (of which Peer Reviewed: 18 results) Presentation (23 results) Book (1 results)

  • [Journal Article] Synthesis of substituted 3-iodopyrroles by cycloisomerization of propargylic aziridines with iodine.2011

    • Author(s)
      Masahiro Yoshida
    • Journal Title

      Tetrahedron

      Volume: 67(印刷中)

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis of cyclic hemiacetals from 4-formylbenzoates and α, β-unsaturated aldehydes using a sulfoalkyl-substituted N-heterocyclic carbene catalyst.2010

    • Author(s)
      M.Yoshida, N.Terai, K.Shishido
    • Journal Title

      Tetrahedron 66

      Pages: 8922-8927

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Highly regioselective synthesis of substituted tetrahydroquinolines by palladium-catalyzed cyclization of substituted 2-amidophenylmalonates with 1,4-diacetoxybut-2-ene.2010

    • Author(s)
      M.Yoshida Y.Maeyama, K.Shishido
    • Journal Title

      Tetrahedron Lett. 51

      Pages: 6008-6010

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Concise and efficient synthesis of 4-hydroxy-2-pyrones from pentane-2, 4-diones.2010

    • Author(s)
      M.Yoshida H.Takai, C.Mitsuhashi, K.Shishido
    • Journal Title

      Heterocycles 81

      Pages: 881-886

    • NAID

      40017418880

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective formal total synthesis of aplysin utilizing a palladium-catalyzed addition of an arylboronic acid to an allenic alcohol-Eschenmoser-Claisen rearrangement.2010

    • Author(s)
      M.Yoshida Y.Shoji, K.Shishido
    • Journal Title

      Tetrahedron 66

      Pages: 5053-5058

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Highly diastereoselective synthesis of tetrahydrobenzofuran derivatives by palladium-catalyzed reaction of propargylic esters with substituted beta-dicarbonyl compounds.2010

    • Author(s)
      M.Yoshida M.Higuchi, K.Shishido
    • Journal Title

      Tetrahedron 66

      Pages: 2675-2682

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] A synthetic study of bauhinoxepin J: Construction of a dibenzo[b,f]oxepin ring system by a DDQ-promoted oxidative dearomatization-cyclization approach.2010

    • Author(s)
      M.Yoshida Y.Maeyama, K.Shishido
    • Journal Title

      Heterocycles 80

      Pages: 623-629

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Highly regioselective synthesis of substituted tetrahydroquinolines by palladium-catalyzed cyclization of substituted 2-amidophenylmalonates with 1,4-diacetoxybut-2-ene.2010

    • Author(s)
      Masahiro Yoshida
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 6008-6010

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective formal total synthesis of aplysin utilizing a palladium-catalyzed addition of an arylboronic acid to an allenic alcohol-Eschenmoser-Claisen rearrangement.2010

    • Author(s)
      Masahiro Yoshida
    • Journal Title

      Tetrahedron

      Volume: 66 Pages: 5053-5058

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of (±)-heliannuol D based on platinum catalyzed regioselective addition of arvlboronic acids to allene.2010

    • Author(s)
      Mayu Osaka
    • Journal Title

      Heterocycles 80

      Pages: 1003-1012

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective construction of substituted chromans by palladium-catalyzed cyclization of propargylic carbonates with 2-(2-hydroxyphenyl)acetates. M.Yoshida2009

    • Author(s)
      M.Higuchi, K.Shishido
    • Journal Title

      Org.Lett. 11

      Pages: 4752-4755

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of substituted 3-iodopyrroles by electrophilic cyclization of propargylic aziridines.2009

    • Author(s)
      M.Yoshida M.Al-Amin, K.Shishido
    • Journal Title

      Tetrahedron Lett. 50

      Pages: 6268-6270

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Oxidative carboxylation of arylaldehydes with water by a sulfoxylalkyl-substituted N-heterocyclic carbene catalyst.2009

    • Author(s)
      M.Yoshida Y.Katagiri, W.-B.Zhu, K.Shishido
    • Journal Title

      Org.Biomol.Chem. 7

      Pages: 4062-4066

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Syntheses of substituted furans and pyrroles by platinum-catalyzed2009

    • Author(s)
      M.Yoshida M.Al-Amin, K.Shishido
    • Journal Title

      cyclizations of propargylic oxiranes and aziridines in aqueous media. Synthesis

      Pages: 2454-2466

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total synthesis of radulanin H and proposed structure of radulanin2009

    • Author(s)
      E.M.Yoshida K.Nakatani, K.Shishido
    • Journal Title

      Tetrahedron 65

      Pages: 5702-5708

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total syntheses of enokipodins A and B utilizing palladium-catalyzed addition of an arylboronic acid to an allene.2009

    • Author(s)
      Masahiro Yoshida
    • Journal Title

      Organic Letters 11

      Pages: 1441-1443

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective construction of substituted chromans by palladium-catalyzed cyclization of propargylic carbonates with 2-(2-hydroxyphenyl)acetates.2009

    • Author(s)
      Masahiro Yoshida
    • Journal Title

      Organic Letters 11

      Pages: 4752-4755

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of substituted 3-iodopyrroles by cycloisomerization of propargylic aziridines with iodine.

    • Author(s)
      M.Yoshida S.Easmin, M.Al-Amin, Y.Hirai, K.Shishido
    • Journal Title

      Tetrahedron in press

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Presentation] パラジウム触媒を用いたプロパルギルエステルとβ-イミノエステルの反応による含窒素複素環化合物の立体選択的合成2011

    • Author(s)
      吉田昌裕、水口智貴、樋口真理子、宍戸宏造
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2010 Final Research Report
  • [Presentation] パラジウム触媒を用いた連続的環化反応による置換テトラヒドロキノリンのエナンチオ選択的合成2011

    • Author(s)
      吉田昌裕、前山陽平、宍戸宏造
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2010 Final Research Report
  • [Presentation] 白金触媒を用いた置換アレンとアリールボロン酸の立体選択的付加環化反応2011

    • Author(s)
      吉田昌裕、庄司康伸、大野祥子、宍戸宏造
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2010 Final Research Report
  • [Presentation] プロパルギル化合物を用いた新規分子変換反応の開発と展開2011

    • Author(s)
      吉田昌裕
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡[招待]
    • Year and Date
      2011-03-29
    • Related Report
      2010 Final Research Report
  • [Presentation] プロパルギル化合物を用いた新規分子変換反応の開発と展開2011

    • Author(s)
      吉田昌裕
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡市
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] Total synthesis of enokipodin A utilizing a palladium-catalyzed addition of an arylboronic acid to an allenic alcohol-Eschenmoser rearrangement Yasunobu Shoji2010

    • Author(s)
      Masahiro Yoshida, Kozo Shishido
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu(USA)
    • Year and Date
      2010-12-19
    • Related Report
      2010 Final Research Report
  • [Presentation] Formal total synthesis of aplysin utilizing a palladium-catalyzed addition of an arylboronic acid to an allenic alcohol-Eschenmoser rearrangement Yasunobu Shoji2010

    • Author(s)
      Masahiro Yoshida, Kozo Shishido
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2010-12-19
    • Related Report
      2010 Final Research Report
  • [Presentation] Synthesis of substituted 3-iodopyrroles by the cyclization of propargylic aziridines2010

    • Author(s)
      Yuuki Hirai, Masahiro Yoshida, Salina Easmin, Mohammad Al-Amin, Kozo Shishido
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2010-12-19
    • Related Report
      2010 Final Research Report
  • [Presentation] Platinum-catalyzed cascade cyclization-ring expansion reaction of propargylic aziridines Yohei Maeyama2010

    • Author(s)
      Masahiro Yoshida, Al-Amin Mohammad, Kozo Shishido
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2010-12-18
    • Related Report
      2010 Final Research Report
  • [Presentation] Stereoselective construction of substituted chromans by palladium-catalyzed cyclization of propargylic carbonates with 2-(2-hydroxyphenyl)acetates2010

    • Author(s)
      Masahiro Yoshida, Mariko Higuchi, Kozo Shishido
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2010-12-18
    • Related Report
      2010 Final Research Report
  • [Presentation] Reactions of arylaldehydes by a sulfoxylalkyl-substituted N-heterocyclic carbene catalyst2010

    • Author(s)
      Masahiro Yoshida, Nagisa Terai, Yuki Katagiri Kozo Shishido
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2010-12-18
    • Related Report
      2010 Final Research Report
  • [Presentation] スルホアルキル置換NHC 触媒を用いたアリールアルデヒドの反応2010

    • Author(s)
      吉田昌裕、寺井渚、片桐由貴、朱文彬、宍戸宏造
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2010-11-01
    • Related Report
      2010 Final Research Report
  • [Presentation] 二価パラジウム錯体を用いたアレンへのアリールボロン酸の付加反応を活用した(-)-aplysin の全合成2010

    • Author(s)
      吉田昌裕、庄司康伸、宍戸宏造
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-30
    • Related Report
      2010 Final Research Report
  • [Presentation] パラジウム触媒を用いたプロパルギルエステルとβ-ケトエステル及びβ-イミノエステルの連続的環化反応2010

    • Author(s)
      吉田昌裕、樋口真理子、宍戸宏造
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-30
    • Related Report
      2010 Final Research Report
  • [Presentation] 二価白金錯体を用いたアレンとアリールボロン酸の連続的付加環化反応2010

    • Author(s)
      吉田昌裕、大野祥子、松田健之介、宍戸宏造
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-29
    • Related Report
      2010 Final Research Report
  • [Presentation] 二価パラジウム錯体を用いたアレンへのアリールボロン酸の付加反応を活用した(+)-helianane の合成研究2010

    • Author(s)
      吉田昌裕、山本佳世、宍戸宏造
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-29
    • Related Report
      2010 Final Research Report
  • [Presentation] プラチナ触媒を用いたプロパルギルアジリジンの連続的環化-環拡大反応2010

    • Author(s)
      吉田昌裕、前山陽平、宍戸宏造
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] Synthesis of substituted 3-iodopyrroles by the cyclization of propargylic aziridines2010

    • Author(s)
      吉田昌裕、Mohammad Al-Amin、SalinaEasmin、宍戸宏造
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] 機能性イミダゾリウムカルベン触媒を用いた芳香族アルデヒドと不飽和アルデヒドの連続反応2010

    • Author(s)
      吉田昌裕、寺井渚、宍戸宏造
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] パラジウム触媒を用いた炭酸プロパルギル化合物の連続反応による多置換クロマンの立体選択的合成2009

    • Author(s)
      吉田昌裕、樋口真理子、宍戸宏造
    • Organizer
      創薬懇話会2009
    • Place of Presentation
      岐阜
    • Year and Date
      2009-12-10
    • Related Report
      2010 Final Research Report
  • [Presentation] パラジウム触媒を用いた炭酸プロパルギルエステルと求核剤の反応による含酸素複素環化合物の立体選択的合成2009

    • Author(s)
      吉田昌裕、樋口真理子、宍戸宏造
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢
    • Year and Date
      2009-11-17
    • Related Report
      2010 Final Research Report
  • [Presentation] パラジウム触媒を用いた炭酸プロパルギルエステルと求核剤の反応による含酸素複素環化合物の立体選択的合成2009

    • Author(s)
      吉田昌裕
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢市
    • Year and Date
      2009-11-17
    • Related Report
      2009 Annual Research Report
  • [Presentation] 白金族金属触媒を用いたアレンへのアリールボロン酸の位置選択的付加反応の開発とEnokipodin 類合成への応用2009

    • Author(s)
      吉田昌裕、庄司康伸、松田健之介、宍戸宏造
    • Organizer
      第96回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2009-11-05
    • Related Report
      2010 Final Research Report
  • [Book] "Transition metal-catalyzed ring expansion cyclization reactions" in Handbook of Cyclization Reactions (Edited by S.-M.Ma)2009

    • Author(s)
      Masahiro Yoshida
    • Total Pages
      39
    • Publisher
      WILEY-VCH
    • Related Report
      2009 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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