Enantioselective total syntheses of novel PKC activator (+)-decursin and its derivatives using catalytic asymmetric epoxidation of an enone

T. Nemoto, T. Ohshima, M. Shibasaki

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Abstract

The catalytic asymmetric total syntheses of (+)-decursin and three related natural products, (+)-decursinol, (-)-prantschimgin and (+)-marmesin, were achieved for the first time using catalytic asymmetric epoxidation of an enone as the key step. The catalytic asymmetric epoxidation of enone was found to be promoted effectively by novel multifunctional asymmetric catalyst generated from La(O-i-Pr)3, BINOL and O=AsPh3 in a 1:1:1 ratio to afford epoxide in 94% yield and 96% ee, which was recrystallized to give the optically pure epoxide. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)9569-9574
Number of pages6
JournalTetrahedron Letters
Volume41
Issue number49
DOIs
Publication statusPublished - Dec 2 2000
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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