Enantioselective total synthesis of (R)-(−)-complanine

Abstract

A route is described for the enantioselective synthesis of (R)-(−)-complanine, a marine natural product isolated from Eurythoe complanata, and known to be a causative agent in inflammation. An organocatalytic, asymmetric oxyamination of a homoconjugated all-Z-dienal intermediate provides versatile and efficient access to the natural product.

Keywords

• complanine
• enantioselective synthesis
• marine fireworm
• nitrosoaldol
• organocatalysis