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Total synthesis of Salinosporamide A, a potent proteasome inhibitor

Research Project

Project/Area Number 18590023
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionDoshisha Women's College of Liberal Arts

Principal Investigator

SHIRAI Ryuichi  Doshisha Women's College of Liberal Arts, 薬学部, 教授 (80183838)

Co-Investigator(Kenkyū-buntansha) SHIMAZAWA Rumiko  同志社女子大学, 薬学部, 専任講師 (00411083)
KURIYAMA Masami  長崎大学, 大学院・医歯薬学総合研究科, 准教授 (40411087)
Project Period (FY) 2006 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥4,100,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥600,000)
Fiscal Year 2008: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2007: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2006: ¥1,500,000 (Direct Cost: ¥1,500,000)
KeywordsSalinosporamide A / プロテアソーム / ピペラジン / 不斉非対称化 / 不斉合成 / 全合成 / 1,2-ジオール / 1,3-ジオール
Research Abstract

Asymmetric desymmetrizations of σ-symmetric 1, 2-diols and 1, 3-diols were successfully achieved with newly developed C_2-symmetric piperadine-type chiral diamine, DMPP.Furthermore a key intermediate for the total synthesis of Salinosporamide A was synthesized in high optical yield by means of the desymmetrization of σ-symmetric 1,3-diol with DMPP-CuCl_2 complex and benzoyl chloride.

Report

(4 results)
  • 2008 Annual Research Report   Final Research Report ( PDF )
  • 2007 Annual Research Report
  • 2006 Annual Research Report
  • Research Products

    (23 results)

All 2009 2008 2007 2006 Other

All Journal Article (10 results) (of which Peer Reviewed: 9 results) Presentation (11 results) Remarks (2 results)

  • [Journal Article] Palladium-Catalyzed 1,2-Addition of Potassium Aryl- and Alkenyltrifluoro borates to Aldehydes using Thioether-Imidazolinium Carbene Ligands2008

    • Author(s)
      Masami Kuriyama, Rumiko Shimazawa, Terumichi Enomoto, Ryuichi Shirai
    • Journal Title

      Journal of Organic Chemistry 73

      Pages: 6939-6942

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Anacid-catalyzed ring-switch reaction of lactums to lactones : concise synthesis of 2,4-dialkyl-3-hydroxybutanolides2008

    • Author(s)
      Chiaki Yamauchi, Masami Kuriyama, Rumiko Shimazawa, Tsumoru Morimoto, Kiyomi Kakiuchi, Ryuichi Shirai
    • Journal Title

      Tetrahedron 64

      Pages: 3133-3140

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Efficient 1,2-Addition of Aryl- and Alkenylboronic Acids to Aldehydes Catalyzed by the Palladium/Thioether-Imidazolinium Chloride System2008

    • Author(s)
      Masami Kuriyama, Rumiko Shimazawa, Ryuichi Shirai
    • Journal Title

      Journal of Organic Chemistry 73

      Pages: 1597-1600

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Direct asymmetric aldol reactions catalyzed by lproline-2,4,6-trinitroanilide2008

    • Author(s)
      Kosuke Sato, Masami Kuriyama, Rumiko Shimazawa, Tsumoru Morimoto, Kiyomi Kakiuchi, Ryuichi Shirai
    • Journal Title

      Tetrahedron Letters 49

      Pages: 2402-2406

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Design and Synthesis of Novel C2-Symmetric Chiral Piperadines and an Application to Asymmetric Acylation of σ-Symmetric 1,2-Diols2008

    • Author(s)
      Daisuke Nakamura, Kiyomi Kakiuchi, Kenji Koga, Ryuichi Shirai
    • Journal Title

      Organic Letters 8

      Pages: 6139-6142

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed 1, 2-addition of potassium aryl-and alkenyltrifluoroborates to aldehydes using thioether- imidazolinium carbene ligands2008

    • Author(s)
      Masami Kuriyama
    • Journal Title

      Journal of Organic Chemistry 73

      Pages: 6939-6942

    • NAID

      130006998727

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An acid-catalyzed ring-switch reaction of lactams to lactones:concise synthesis of 2,4-dialky1-3-hydroxybutanolides2008

    • Author(s)
      Chiaki Yamauchi
    • Journal Title

      Tetrahedron 64

      Pages: 3133-3140

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient 1,2-addition of aryl-and alkenylboronic acids to aldehydes catalyzed by the palladium/thioether-imidazolium chloride system2008

    • Author(s)
      Masami Kuriyama
    • Journal Title

      Journal of Organic Chemistry 73

      Pages: 1579-1600

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct asymmetric aldol reactions catalyzed by L-proline-2,4,6-trinitroanilide2008

    • Author(s)
      Kosuke Sato
    • Journal Title

      Tetrahedron Letters 49

      Pages: 2402-2406

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design and Synthesis of Novel C_2-Symmetric Chiral Piperazines and an Application to Asymmetric Acylation of σ-Symmetric 1,2-Diols2006

    • Author(s)
      Daisuke Nakamura
    • Journal Title

      Organic Letters 8・26

      Pages: 6139-6142

    • Related Report
      2006 Annual Research Report
  • [Presentation] C-S二座配位子-パラジウム触媒による有機ホウ酸試薬のキラルアルデヒドへのジアステレオ選択的1,2-付加反応2009

    • Author(s)
      榎本光伯, 栗山正巳, 白井隆一
    • Organizer
      日本薬学会129年会
    • Place of Presentation
      国立京都国際会館
    • Year and Date
      2009-03-26
    • Related Report
      2008 Final Research Report
  • [Presentation] C- S二座配位子-パラジウム触媒による有機ホウ酸試薬のキラルアルデヒドヘのジアステレオ選択的1, 2-付加反応2009

    • Author(s)
      榎本光伯
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      国立京都国際会館
    • Year and Date
      2009-03-26
    • Related Report
      2008 Annual Research Report
  • [Presentation] C-S二座配位子-パラジウム触媒を用いた有機三フッ化ホウ素塩のアルデヒドへの付加反応2008

    • Author(s)
      栗山正巳, 石山夏希, 榎本光伯, 嶋澤るみ子, 白井隆一, 尾野村治
    • Organizer
      反応と合成の進歩シンポジウム
    • Place of Presentation
      京都テルサ
    • Year and Date
      2008-11-04
    • Related Report
      2008 Annual Research Report 2008 Final Research Report
  • [Presentation] C-S二座配位子-パラジウム触媒による有機ホウ酸試薬のキラルアルデヒドへのジアステレオ選択的1,2-付加反応2008

    • Author(s)
      榎本光伯, 栗山正巳, 白井隆一
    • Organizer
      第58回日本薬学会近畿支部総会・大会
    • Place of Presentation
      神戸薬科大学
    • Year and Date
      2008-10-25
    • Related Report
      2008 Final Research Report
  • [Presentation] C-S二座配位子-パラジウム触媒を用いた有機三フッ化ホウ素塩のアルデヒドへの付加反応2008

    • Author(s)
      栗山正巳, 嶋澤るみ子, 榎本光伯, 白井隆一
    • Place of Presentation
      神戸薬科大学
    • Year and Date
      2008-10-25
    • Related Report
      2008 Final Research Report
  • [Presentation] C- S二座配位子- パラジウム触媒を用いた有機三フッ化ホウ素塩のアルデヒドへの付加反応2008

    • Author(s)
      栗山正巳
    • Organizer
      第58回日本薬学会近畿支部総会・大会
    • Place of Presentation
      神戸薬科大学
    • Year and Date
      2008-10-25
    • Related Report
      2008 Annual Research Report
  • [Presentation] C-S二座配位子-パラジウム触媒による有機ホウ酸試薬のキラルアルデヒドヘのジアステレオ選択的1, 2-付加反応2008

    • Author(s)
      榎本光伯
    • Organizer
      第58回日本薬学会近畿支部総会・大会
    • Place of Presentation
      神戸薬科大学
    • Year and Date
      2008-10-25
    • Related Report
      2008 Annual Research Report
  • [Presentation] 複素環カルベンを基盤とするC-S二座配位子-パラジウム触媒による有機ホウ素試薬を用いたアルデヒドへの付加反応2008

    • Author(s)
      栗山正巳, 嶋澤るみ子, 白井隆一
    • Organizer
      日本薬学会128年会
    • Place of Presentation
      パシフィコ横浜
    • Year and Date
      2008-03-26
    • Related Report
      2008 Final Research Report
  • [Presentation] 複素環カルベンを基盤とするC-S二座配位子-パラジウム触媒による有機ホウ素試薬を用いたアルデヒドへの付加反応2008

    • Author(s)
      栗山 正巳
    • Organizer
      日本薬学会第128年会
    • Place of Presentation
      パシフィコ横浜
    • Year and Date
      2008-03-26
    • Related Report
      2007 Annual Research Report
  • [Presentation] 複素環カルベンを基盤とするC-S二座配位子-パラジウム触媒による有機ホウ素試薬を用いたアルデヒドへの付加反応2007

    • Author(s)
      栗山正巳, 嶋澤るみ子, 白井隆一
    • Organizer
      第57回日本薬学会近畿支部総会・大会
    • Place of Presentation
      大阪薬科大学
    • Year and Date
      2007-10-27
    • Related Report
      2008 Final Research Report
  • [Presentation] 複素環カルベンを基盤とするC-S二座配位子-パラジウム触媒による有機ホウ素試薬を用いたアルデヒドへの付加反応2007

    • Author(s)
      栗山 正巳
    • Organizer
      第57回日本薬学会近畿支部大会・総会
    • Place of Presentation
      大阪薬科大学
    • Year and Date
      2007-10-27
    • Related Report
      2007 Annual Research Report
  • [Remarks] ホームページ

    • URL

      http://www.dwc.doshisha.ac.jp/research/data/915.html

    • Related Report
      2008 Final Research Report
  • [Remarks]

    • URL

      http://www.dwc.doshisha.ac.jp/research/data/915.html

    • Related Report
      2008 Annual Research Report

URL: 

Published: 2006-04-01   Modified: 2016-04-21  

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