A Metathesis–Acylation Approach to the Bicyclic Core of Polycyclic Poly­prenylated Acylphloroglucinols

Abstract

An approach to a model compound for polycyclic polyprenylated acylphloroglucinols is developed using a ring-closing metathesis approach to give a substituted cyclooctene. This undergoes cyclization via an intramolecular acylation leading to a substituted bicyclo[3.3.1]nonan-9-one related to hyperforin, nemorosone, clusianone, garsubellin A and other members of the polyprenylated acylphloroglucinol.

Key words

bicyclic compounds - natural products - metathesis - alkene acylation - steric hindrance

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