Synthesis of 11-Acetoxy-4-deoxyasbestinin D

Significance

Isolated from Briareum asbestinum in 1990, 11-acetoxy-4-deoxyasbestinin D displays significant cytotoxic and antimicrobial activity. Crimmins and Ellis employed a ring-closing metathesis/intramolecular Diels-Alder cycloaddition strategy to synthesize the oxonene ring and hydroisobenzofuran system, respectively, providing the first chemical synthesis of any member of this family of cembranoids and thus establishing their absolute configuration. A related synthesis of Ophirin B and Astrogorgin has appeared recently: M. T. Crimmins, B. H. Brown, H. R. Plake J. Am. Chem. Soc. 2006, 128, 1371-1378.