Stereoselective approach to the DEF ring system of terpendole e

Takaaki Teranishi, Shigefumi Kuwahara

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Diastereoselective construction of a DEF ring model of terpendole E, a M phase-specific antimitotic natural product, has been achieved from a known bicyclic keto ester by a 10-step (or 12-step) sequence that features an efficient one-pot intramolecular etherification of an olefinic alcohol with mCPBA. The synthesis proceeded in an excellent overall yield of 36% through 10 steps or in 56% via 12 steps which involved a highly diastereoselective reduction of a ketone derived from an undesired diastereomeric alcohol intermediate.

Original languageEnglish
Pages (from-to)1486-1487
Number of pages2
JournalTetrahedron Letters
Volume55
Issue number8
DOIs
Publication statusPublished - 2014 Feb 19

Keywords

  • Antimitotic
  • Epoxidation
  • Indole diterpene
  • Terpendole
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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