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Efficient Synthesis of the alkyl chains with multiple stereogenic centers

Research Project

Project/Area Number 21655035
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionWaseda University

Principal Investigator

HOSOKAWA Seijiro  早稲田大学, 理工学術院, 准教授 (10307712)

Co-Investigator(Kenkyū-buntansha) TATSUTA Kuniaki  早稲田大学, 名誉教授・栄誉フェロー (40051627)
Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥3,470,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥270,000)
Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2010: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2009: ¥1,300,000 (Direct Cost: ¥1,300,000)
Keywords有機合成化学 / 不斉合成 / 鎖状化合物 / ポリケチド / 遠隔不斉誘導 / 天然物合成 / 不斉素子 / 鎖状立体制御
Research Abstract

Two subjects shown below have been successfully performed.
(1) Development of remote asymmetric induction methodologies by using chiral vinylketene N, O-acetals
The chiral vinylketene N, O-acetal, derived from α-methyl-α,β-unsaturated imide, was found to give syn adduct stereoselectively by the Lewis-acid mediated aldol reaction with acetals. The same N, O-acetal also gave syn adducts by reaction with aldehyde and excess amount of TiCl_4. This N, O-acetal has already known to afford anti adducts stereoselectively by reacting with aldehyde and one equivalent of TiCl_4.Therefore, we established stereo-divergent synthesis ofδ-alkoxy-γ-methyl-α,β-unsaturated imide by choosing amount of TiCl_4.The chiral vinylketene N, O-acetal has reacted with acid anhydrides to proceed acylation, the 1, 6-asymmetric induction reaction. Additionally, the chiral vinylketene N, O-acetal without the α-methyl group also performed the remote asymmetric induction.
(2) Synthesis of polyketide haing multiple stereogenic centers
The adducts of the remote asymmetric induction reaction mentioned above have been submitted to the regio-and stereoselevtive reduction to give methyl-branched fatty acids with desired stereochemistry.
The adduct of the chiral vinylketene N, O-acetal and an α-methyl-α,β-unsaturated aldehyde has both allylic alcohol and the α,β-unsaturated imide. Taking advantage of the adduct, we have realized the regio-and stereoselective reduction and established the short step synthesis of reducted polyketide chains.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (12 results)

All 2012 2011 2009 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (7 results) Book (1 results) Remarks (2 results)

  • [Journal Article] The first total synthesis and structural determination of benzopyrenomycin2009

    • Author(s)
      Seijiro Hosokawa, 他3名
    • Journal Title

      Tetrahedron Letters 50

      Pages: 6701-6704

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The first total synthesis of nidulalin A, a dihydroxanthone possessing multiple bioactivities2009

    • Author(s)
      Kuniaki Tatsuta, Seijiro Hosokawa, 他3名
    • Journal Title

      Journal of Antibiotics 62

      Pages: 469-470

    • NAID

      10030636165

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] アセタールを用いたsyn選択的なビニロガス向山アルドール反応の開発2012

    • Author(s)
      塚田洋之・迎田裕貴・細川誠二郎
    • Organizer
      日本化学会第92春季年会(2012)
    • Place of Presentation
      神奈川
    • Year and Date
      2012-03-28
    • Related Report
      2011 Annual Research Report
  • [Presentation] 新型ビニロガス向山アルドール反応の開発研究2012

    • Author(s)
      迎田裕貴・佐川直也・細川誠二郎
    • Organizer
      日本化学会第92春季年会(2012)
    • Place of Presentation
      神奈川
    • Year and Date
      2012-03-28
    • Related Report
      2011 Annual Research Report
  • [Presentation] ポリケチド鎖の立体選択的構築法の開発2012

    • Author(s)
      加野孝明・中村竜也・迎田裕貴・細川誠二郎
    • Organizer
      日本化学会第92春季年会(2012)
    • Place of Presentation
      神奈川
    • Year and Date
      2012-03-28
    • Related Report
      2011 Annual Research Report
  • [Presentation] アセタールを用いたsyn選択的なビニロガス向山アルドール反応の開発2012

    • Author(s)
      塚田洋之・迎田裕貴・細川誠二郎
    • Organizer
      日本化学会第92春季年会
    • Related Report
      2011 Final Research Report
  • [Presentation] 新型ビニロガス向山アルドール反応の開発研究2012

    • Author(s)
      迎田裕貴・佐川直也・細川誠二郎
    • Organizer
      日本化学会第92春季年会
    • Related Report
      2011 Final Research Report
  • [Presentation] ポリケチド鎖の立体選択的構築法の開発2012

    • Author(s)
      加野孝明・中村竜也・迎田裕貴・細川誠二郎
    • Organizer
      日本化学会第92春季年会
    • Related Report
      2011 Final Research Report
  • [Presentation] 抗腫瘍性物質 Benzopyrenomycin の全合成2009

    • Author(s)
      細川誠二郎, 迎田裕貴, 川原領, 竜田邦明
    • Organizer
      第96回 有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2009-11-06
    • Related Report
      2009 Annual Research Report
  • [Book] 天然物合成で活躍した反応2011

    • Author(s)
      竜田邦明、細川誠二郎
    • Publisher
      化学同人
    • Related Report
      2011 Final Research Report
  • [Remarks] 研究室HP

    • URL

      http://www.waseda.jp/sem-hosokawalab

    • Related Report
      2011 Final Research Report
  • [Remarks] Thieme Chemistry Journals Award 2010 受賞

    • Related Report
      2009 Annual Research Report

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

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