Synthesis of an advanced intermediate enroute to (−)-clavosolide A

A stereoselective route to an advanced intermediate toward the synthesis of clavosolide A is disclosed. The key steps include Wadsworth-Emmons cyclopropanation, utilization of a sulfinyl moiety as an internal nucleophile to open a cyclopropane ring activated by Hg(II)- to create the C3-C5 stereogenic centers, CC bond formation employing an α-chloro sulfide, asymmetric transfer hydrogenation, regioselective hydrosilylation and Tamao-Fleming oxidation.