Studies toward the total synthesis of garsubellin A: synthesis of 8-deprenyl-garsubellin A

During studies directed toward the total synthesis of garsubellin A, synthesis of 8-deprenyl-garsubellin A, containing three (of four in the natural product) stereocenters with the proper configurations, was achieved. Key steps are a one-pot lactone formation, a formal migration to the bicyclo[3.3.1]nonane-1,3,5-trione, and an intramolecular Wacker-type tetrahydrofuran formation.