A STEREOSELECTIVE PI-CYCLIZATION TO A COMBINED BRIDGEHEAD OLEFIN-BRIDGEHEAD ALCOHOL

U VOGT, U EGGERT, A M Z SLAWIN, D J WILLIAMS, H M R HOFFMANN

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

Bridgehead olefin and bridgehead alcohol units are formed simultaneously in one molecule upon solvolysis of the mesylate to give 2 (R = H). The synthesis of 1 from caryophyllene epoxide was achieved for the first time stereoselectively and in good yields. An X-ray structure analysis of the 4-bromobenzoate of 2 confirms the structural assignment.

Original languageEnglish
Pages (from-to)1456-1457
Number of pages2
JournalAngewandte Chemie International Edition in English
Volume29
Issue number12
Publication statusPublished - Dec 1990

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