Stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade

Tomohiro Fujii, Masahisa Nakada

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade is described. The substrate, a ten-membered carbocyclic ketone, has been successfully prepared by the Cr-mediated intramolecular alkenylation of the corresponding acyclic compound. The array of functionalities in the product stereoselectively obtained by the cascade reaction is useful for further structural modifications directed toward the total synthesis of fusidane and other triterpenes, and designed molecules intended for studying structure-activity relationships.

Original languageEnglish
Pages (from-to)1597-1601
Number of pages5
JournalTetrahedron Letters
Volume55
Issue number9
DOIs
Publication statusPublished - 2014 Feb 26

Keywords

  • Fusidane
  • Intermolecular
  • Michael reaction
  • Stereoselective
  • Transannular

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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