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STUDIES OF BIOLOGICALLY ACTIVE NATURAL PRODUCTS CONTAINING PYRROLO [2,3-b] INDOLE UTILIZED THE ASYMMETRIC TANDEM REACTIONS

Research Project

Project/Area Number 09672171
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionMEIJI PHARMACEUTICAL UNIVERSITY

Principal Investigator

KAWASAKI Tomomi  FACULTY OF PHARMACY,MEIJI PHARMACEUTICAL UNIVERSITY ASSOCIATE PROFESSOR, 薬学部, 助教授 (70161304)

Co-Investigator(Kenkyū-buntansha) SAKAMOTO Masanori  FACULTY OF PHARMACY,MEIJI PHARMACEUTICAL UNIVERSITY PROFESSOR, 薬学部, 教授 (70087774)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1998: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1997: ¥1,400,000 (Direct Cost: ¥1,400,000)
Keywordspyrrolo [2,3-b] indole / flustramine C / Claisen rearrangement / olefination / 2-allyloxyindolin-3-one / asymmetric Claisen rearrangement / optically active ylide / optically active allyl alcohol / ピロロ[2,3-b]インドール / 連続反応
Research Abstract

In our studies on total synthesis of alkaloids, aldeemin, amiauromine, flustramine, and peudophynrynaminol, consisting the pyrrolo[2,3-b]indole structure, we have succeeded in synthesis of the desired 3a-allylpyrrolo[2,3-b]indole and in first total synthesis of marine natural product, flustramine C ;
1.We found the new methodology for synthesis of 3a-allylpyrrolo[2,3-b]indole ; the tandem reactions, olefination, isomerization, and Claisen rearrangement of 2-(3,3-dimethylallyl)indolin-3-one produced 3,3-disubstituted oxindole, which was reduced to give 3a-(1, 1-dimethylallyl)-pyrrolo[2,3-b]indole. We succeeded in the first total synthesis of marine natural product, flustramine C utilizing our methodology.
2.The tandem reactions introduced directly two different substituents to 3-site of indole nucleus, and this procedure is a general method for synthesis of 3,3-disubstituted oxindoles.
3.The asymmetric version of the above-mentioned tandem reactions was tried ; olefination, isomerization and Claisen rearrangement of optically active 2-allylindolin-3-one, which was derived from optical active allyl alcohol and 2-bromoindolin-3-one, proceeded stereoselectively to give optically active oxindole in good yield.
4.The reaction of a several kind of 2-allylindolin-3-ones with optically active ylides, followed by isomerization to proceed diastereoselective Claisen rearrangement to afford the oxindole, of which diastereomers were easily separated by silica gel column chromatography to give optically active oxindoles.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (3 results)

All Other

All Publications (3 results)

  • [Publications] T.Kawasaki 等: "A Short Route to “Reverse-Prenylated" Pyrrolo[2, 3-b]indoles via Tandem Olefination and Claisen Rearrangement of 2-(3, 3-Dimethylallyloxy)indol-3-ones : First Total Synthesis of Flustramine C" Tetrahedron Lett.37. 7525-7528 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Kawasaki, R.Terashima, K.Sakaguchi, H.Sekiguchi, and M.Sakamoto: "A Short Route to "Reverse-Prenylated" Pyrrolo [2,3-b] indoles via Tandem Olefination and Claisen Rearrangement of 2-(3,3-Dimethylallyloxy)-indol-3-ones : First Total Synthesis of Flustramine C" Tetrahedron Lett.37. 7528-7525 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Kawasaki 等: "A Short Route to “Reverse-Prenylated"Pyrrolo[2,3-b]indoles via Tandem Olefination and Claisen Rearrangement of 2-(3,3-Dimethylallyloxy)indol-3-ones: First Total Synthesis of Flustramine C" Tetrahedron Lett.37. 7525-7528 (1996)

    • Related Report
      1998 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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