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

Cite this

New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction. / Tokuzaki, Kazuo; Kanemitu, Yasuhiro; Yoshimitsu, Takehiko; Nagaoka, Hiroto.

In: Tetrahedron Letters, Vol. 41, No. 31, 29.07.2000, p. 5923-5926.

Research output: Contribution to journalArticle

Tokuzaki, Kazuo ; Kanemitu, Yasuhiro ; Yoshimitsu, Takehiko ; Nagaoka, Hiroto. / New route to the synthesis of the illudane skeleton by Michael-Michael- elimination reaction. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 31. pp. 5923-5926.
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