Synthetic approaches to mycorrhizin a and gilmicolin. II early introduction of a C3 side chain into a benzofuranol precursor

Abstract

An attempt to modify the previously reported synthesis1 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. © 1983, CSIRO. All rights reserved.