An efficient method for construction of the angularly fused 6,3,5-tricyclic skeleton of mycorrhizin A and its analogues.

ABSTRACT

The angularly fused 6,3,5-tricyclic system is readily generated via a cascade cyclization under acid promotion. The reaction proceeds at room temperature with high stereochemical fidelity from the electrophilic center of the epoxide to the cyclopropane product. This methodology provides a potentially useful approach for the synthesis of mycorrhizin A and its analogues.