Intramolecular nitrile oxide cycloaddition route to carbocyclics: A formal total synthesis of PGF

Alan P. Kozikowski, Philip D. Stein

Research output: Contribution to journalArticle

Abstract

A formal total synthesis of the prostaglandin F is reported which is based on the reaction of a nitrile oxide, generated by the sodium hypochlorite oxidation of an oxime, with a tethered olefin. The present study reveals the importance of an existing ring structure to control both the kinetics and the stereochemical course of the cycloaddition process. The possibility of carrying out the present synthesis in a chiral-selective fashion through employment of a chiral epoxide is also discussed.

Original languageEnglish (US)
Pages (from-to)2301-2309
Number of pages9
JournalJournal of Organic Chemistry
Volume49
Issue number13
DOIs
StatePublished - Jan 1984

ASJC Scopus subject areas

  • Organic Chemistry

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