Synthetic approaches tb mycorrhizin A and gilmicolin. II. Early introduction of a C₃ side chain into a benzofuranol precursor

Abstract

An attempt to modify the previously reported synthesis of the tricyclic system (1) of mycorrhizin A (2) and gilmicolin (3) by very early introduction of a C₃ side chain is described. However, both 6-(2-acetoxypropyl)-7a-methoxy-2,2-dimethylbenzofuran-4,7(2H,7aH)-dione (21) and the corresponding 6-allyl compound (24) fail to add cyclopentadiene as required for protection of the enedione system in the original scheme.