Total synthesis of madindoline A

S. Hosokawa, K. Sekiguchi, K. Hayase, Y. Hirukawa, S. Kobayashi

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The total synthesis of madindoline A was achieved. The key step of the synthesis is a reductive coupling of an acid-sensitive hydroxyfuroindoline derivative and a sterically hindered aldehyde using Sn(OTf)2-NaBH(OAc)3. After the reductive coupling, the derived trione was subjected to intramolecular condensation to construct a madindoline skeleton. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)6435-6439
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number33
DOIs
Publication statusPublished - 2000 Aug 12
Externally publishedYes

Keywords

  • Intramolecular condensation
  • Madindoline A
  • Reductive coupling
  • Tin(II) triflate
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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  • Cite this

    Hosokawa, S., Sekiguchi, K., Hayase, K., Hirukawa, Y., & Kobayashi, S. (2000). Total synthesis of madindoline A. Tetrahedron Letters, 41(33), 6435-6439. https://doi.org/10.1016/S0040-4039(00)00939-4