Macrocyclization through Radical-Mediated Vinylcyclopropane/Alkene Condensation. Facile Entry into the Brefeldin Ring System

Ken S. Feldman, Heidi M. Berven, Anthony L. Romanelli, Masood Parvez

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

Bicyclic products featuring an 11-membered ring fused to a core vinylcyclopentane unit are produced upon treatment of functionalized vinylcyclopropanes bearing an ω-alkene unit with a catalytic amount of phenylthio radical. This intramolecular extension of a radical-mediated vinylcyclopropane/alkene cyclocondensation proceeds with only modest diastereoselectivity. The reaction products resemble members of the brefeldin family of naturally occurring antibiotics.

Original languageEnglish (US)
Pages (from-to)6851-6856
Number of pages6
JournalJournal of Organic Chemistry
Volume58
Issue number24
DOIs
StatePublished - Jan 1 1993

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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