TOTAL SYNTHESIS OF THE PENTACYCLOPROPANE ANTIFUNGAL AGENT FR-900848

Quatercyclopropane 31 was oxidized, homologated, reduced, and monocycl opropanated to provide the pentacyclopropane alcohol 35. Subsequent de oxygenation of alcohol 35 was effected using N-(phenylthio)succinimide (24) and tributylphosphine followed by Raney nickel desulfurization a nd deprotection to produce the alcohol 3. This was oxidized, homologat ed, and hydrolyzed to provide the fatty acid 2. BOP-Cl-mediated coupli ng of acid 2 and the nucleoside amine 40 gave amide 1, which was spect roscopically identical with an authentic sample of FR-900848 (1).