Asymmetric Heck Reaction: Catalytic Asymmetric Syntheses of Bicyclic Enones, Dienones and the Key Intermediate for Vernolepin

Bicyclic enone 23a, a functionalized decalin derivative, has been synthesized in up to 86% ee by an asymmetric Heck reaction starting with bisallylic alcohol 24. Enone 23a has been converted to 19, a key intermediate in the synthesis of vernolepin (14). Furthermore, bicyclic dienone 43 has been synthesized in up to 83% ee from the prochiral dienone 39.