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The Total Synthesis of (±)-Isocomene by an Intramolecular Ene Reaction. Preliminary communication

✍ Scribed by Wolfgang Oppolzer; Kurt Bättig; Tomas Hudlicky

Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
233 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The racemic sesquiterpene isocomene (1) has been synthesized starting from 1,7‐octadien‐3‐one (2) in a stereoselective manner (Scheme 2). In the key step 4 → 5 the C(7), C(8)‐bond was formed by an intramolecular thermal ene reaction. Further elaboration of 5 involved the ring contraction 6 → 7, the elimination 8 → 9 and the final olefin isomerization 9 → 1.

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