Stereoselective Synthesis of the Core Ring System of Lancifonins A-D

Org Lett. 2025 Apr 4;27(13):3123-3127. doi: 10.1021/acs.orglett.5c00263. Epub 2025 Mar 24.

Abstract

A 5/5/7 tricyclic intermediate bearing an oxa-bridged hemiketal ring was successfully synthesized from dihydrocarvone in 14 steps, which is a common intermediate of various Schisandra nortriterpenoids. Subsequently, the core structure of lancifonins A-D, characterized by a 5/5/7/8 fused ring system, was constructed in seven steps. The route employs key transformations, including the aldol reaction, Mukaiyama hydration, Mn(III)-mediated cyclization, the Suzuki reaction, and McMurry coupling.