A synthetic approach directed towards the synthesis of the clerodane diterpene bacchofertin.

摘要

Bacchofertin, an ent-Clerodane diterpene, is a member of a very large family of natural products that are known to poses biological activities ranging from antibacterial, antimicrobial, antiulcer, to insect antifeedants. These are highly substituted decalin rings differing from one another by the presence or absence of an oxygen functionality at various sites on the ring. Presented herein are synthetic steps directed towards a synthesis of Bacchofertin. The key feature in the synthetic venture is the utilization of a Lewis acid catalyzed intramolecular cycloaddition to yield a tricyclic ring. This reaction allows for stereochemical control at various sites on the ring. Oxidative unraveling of the tricyclic ring unmasks the decalin ring and provides a handle for introducing oxygen functionality.