Synthesis of Novel 6β,14-Epoxy-Bridged Opiates

K. E. MaloneyHuss, P. S. Portoghese

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

During the course of our research directed toward the development of selective opioid receptor antagonists, we discovered a novel opiate cyclization that makes the opiate C-ring rigid in a manner similar to the oripavines l.1 These new compounds (2a, 2b) have a 6,14/3-epoxy linkage in place of the 6,14/3-ethano bridge of Bently's1 extremely potent thebaine-derived oripavines 1. This was accomplished by an intramolecular ether-forming reaction of the relatively flexible C ring of 6a-(mesyloxy) opiates 4a and 4b, converting them into the rigid 1,4-epoxycyclohexane derivatives 2a and 2b.

Original languageEnglish (US)
Pages (from-to)2957-2959
Number of pages3
JournalJournal of Organic Chemistry
Volume55
Issue number9
DOIs
StatePublished - Jan 1 1990

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