New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction

Kazuo Tokuzaki, Yasuhiro Kanemitu, Takehiko Yoshimitsu, Hiroto Nagaoka

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

A new route to the synthesis of an optically active illudane skeleton from (R)-(-)-pantolactone (4) is established. The tricyclic ring system was constructed by Michael-Michael-elimination reaction of the enolate of (3S,5R)-3-(tert-butyldimethylsilyloxy)-5-methoxymethyloxy-1- propionylcyclopentene (10) with ethyl cyclopropylidenacetate (3).

Original languageEnglish
Pages (from-to)5923-5926
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number31
DOIs
Publication statusPublished - Jul 29 2000
Externally publishedYes

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Keywords

  • Antitumor compounds
  • Michael reactions
  • Terpenes and terpenoids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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