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1998 Fiscal Year Final Research Report Summary

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
Keywordspyrrolo [2,3-b] indole / flustramine C / Claisen rearrangement / olefination / 2-allyloxyindolin-3-one / asymmetric Claisen rearrangement / optically active ylide / optically active allyl alcohol
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.

  • Research Products

    (2 results)

All Other

All Publications (2 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
  • [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

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Published: 1999-12-08  

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