Construction of the Benzylic Quaternary Carbon Center of Zoanthenol by Intramolecular Mizoroki - Heck Reaction of Enone

Go Hirai, Yuuki Koizumi, Sameh M. Moharram, Hiroki Oguri, Masahiro Hirama

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

(matrix presented) Stereocontrolled synthesis of the ABC ring framework of zoanthenol has been achieved. Our studies show that a ββ-substituted enone can act as a good acceptor of arylpalladium intermediates in the formation of a congested benzylic quaternary carbon center through an intramoleculer Mizoroki-Heck reaction. The cis B/C ring system was stereoselectively converted to the trans-fused framework through a Sml2-promoted deoxygenation of the α-hydroxy ketone.

Original languageEnglish
Pages (from-to)1627-1630
Number of pages4
JournalOrganic Letters
Volume4
Issue number9
DOIs
Publication statusPublished - May 2 2002
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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