Total synthesis of the Isodon diterpene sculponeatin N

Abstract

The total synthesis of sculponeatin N, a bioactive polycyclic diterpene isolated from Isodon sculponeatus, is reported. Key features of the synthesis include diastereoselective Nazarov and ring-closing metathesis reactions, and a highly efficient formation of the bicyclo[3.2.1]octane ring system by a reductive radical cyclization.

Keywords: isodon terpenes; natural products; reductive cyclization; ring-closing metathesis.