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Synthesis of 1-substituted tetrahydroisoquinoline alkaloid utilizing intramolecular chirality transfer reaction

Research Project

Project/Area Number 26460020
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionMukogawa Women's University

Principal Investigator

Kawai Nobuyuki  武庫川女子大学, 薬学部, 講師 (10411034)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords分子内不斉転写 / 触媒 / 1位置換テトラヒドロイソキノリン / 過塩素酸 / アルカロイド合成 / 1,3-不斉転写 / 光学活性1位置換テトラヒドロイソキノリン / 過塩素酸触媒 / シュルゼインのベンゾキノリジン骨格 / benzo[a]quinolizidine環 / Schulzeine / 形式合成 / テトラドロイソキノリン / 不斉転写
Outline of Final Research Achievements

Intramolecular chirality transfer reaction is one of useful reactions for synthesizing chiral cyclic compounds. Although the Bi(OTf)3 have been reported to be effective catalyst for the synthesis of 1-substituted tetrahydrioquinolines from chiral amino allylic alcohols, there are some limitations such as failure to synthesize 8-substituted derivatives with high optical purity. In this research, HClO4 found to be most effective catalyst replacing Bi(OTf)3. Furthermore, formal synthesis of alkaloid, Schultzain B, has been accomplished through the construction of a tetrahydroisoquinoline ring having substituents at the 6th and 8th positions.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (4 results)

All 2015 2014

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

  • [Journal Article] Synthesis of optically pure (R)- and (S)-tetrahydroisoquinoline-1- and -3-carboxylic acids2015

    • Author(s)
      Kurata, Kaoruko; Inoue, Kumiko; Nishimura, Kazuhiko; Hoshiya, Naoyuki; Kawai, Nobuyuki; Uenishi, Junichi
    • Journal Title

      Synthesis

      Volume: 47 Issue: 09 Pages: 1238-1244

    • DOI

      10.1055/s-0034-1380289

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis of the Core Tricyclic Ring Domain of (–)-Schulzeine B2015

    • Author(s)
      Naoyuki Hoshiya, Kenta Noda, Yuji Mihara, Nobuyuki Kawai, Jun’ichi Uenishi
    • Journal Title

      Journal of Organic Chemistry

      Volume: 80 Issue: 15 Pages: 7790-7796

    • DOI

      10.1021/acs.joc.5b01173

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] 光学活性1-アルケニルテトラヒドロイソキノリンから有用アミノ化合物への変換2014

    • Author(s)
      野田健太、倉田薫子、三原裕二、西村和晃、河井伸之、星谷尚亨、上西潤一
    • Organizer
      第44回複素環化学討論会
    • Place of Presentation
      札幌市民ホール(北海道・札幌市)
    • Year and Date
      2014-09-10 – 2014-09-12
    • Related Report
      2014 Research-status Report
  • [Book] 化学構造と薬理作用 医薬品を化学的に読む 第2版2015

    • Author(s)
      監修:柴崎正勝, 赤池昭紀, 橋田充
    • Total Pages
      496
    • Publisher
      廣川書店
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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