Biomimetic Asymmetric Total Synthesis of (-)-Laurefucin via an Organoselenium-Mediated Intramolecular Hydroxyetherification

Abstract

The first asymmetric total synthesis of (-)-laurefucin (1), a unique C-15 acetogenin with a 2,8-dioxabicyclo[5.2.1]decane skeleton, has been accomplished in nine steps in 31% overall yield from known oxocene 10. Highlights of the highly stereoselective synthesis include a novel organoselenium-mediated biomimetic hydroxyetherification.