A total synthesis of (±)-isocomene and (±) β-isocomene by an intramolecular ene reaction

W Oppolzer, K Bättig, T Hudlicky

Index: Oppolzer, W.; Baettig, K.; Hudlicky, T. Tetrahedron, 1981 , vol. 37, # 25 p. 4359 - 4364

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Citation Number: 59

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.