A total synthesis of (±)-isocomene and (±) β-isocomene by an intramolecular ene reaction |
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Authors: | W. Oppolzer, , K. B ttig,T. Hudlicky |
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Affiliation: | Département de Chimie Organique, Université de Genève, CH-1211 Genève 4, Switzerland |
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Abstract: | The racemic sesquiterpenes isocomene 1 and β-isocomene 22 have been synthesized starting from 1,7-octadien-3-one 10 in a stereoselective manner. In the key step 12 → 13 (Scheme 5) the C-7, C-8-bond was formed by an intramolecular thermal ene reaction. Further transformations of 13 (Scheme 6) involved successively ring contraction 18 → 19, elimination 21 → 22 and olefin isomerization 22 → 1. |
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