97. Application of the intramolecular magnesium-ene reaction to the stereocontrolled total syntheses of (±)-12-acetoxysinularene and (±)-5-epi-12-acetoxysinularene
    Oppolzer, W.; Begley, T.; Ashcroft, A.
    Tetrahedron Lett. 1984, 25, 825-828

The sesquiterpene (±)-12-acetoxysinularene (1) and its C(5)-epimer (13) were each synthesized stereoselectively from the norbornyl-iodoacetal 7 in 5% and 7% overall yields. The critical step (10) → (11) involves the regio- and stereoselective “magnesium-ene” reaction (6) → (5).

DOI : 10.1016/S0040-4039(01)80037-X