Preparation of oxocene terpenes. The first enantiospecific synthesis of cytotoxic arenaran A

Abstract

The first syntheses of cytotoxic marine arenarans A and B starting from commercial (−)-sclareol are reported. The oxocene ring of the target compound is formed via ring-closing metathesis, a process that depends on certain structural requirements. The trans-fused structure of the natural product is confirmed by comparison with the cis-fused isomer, which was synthesized. This synthetic strategy is also applicable to the synthesis of other oxocene terpenes.