Total synthesis of maoecrystal V

Abstract

Maoecrystal V (1) is a novel diterpenoid, which was originally isolated from the leaves of the Chinese medicinal herb Isodon eriocalyx in 2004 by Sun et al.1 It has been found to be selectively cytotoxic towards HeLa cells, with an IC50 value of 20 ng mL(-1) . Significant research efforts have been devoted to the synthesis of maoecrystal V because of its intriguing biological properties, rarity in nature, and complex structural features. Herein, we describe our recent investigations, which have culminated in the total synthesis of (±)-maoecrystal V. The current strategy involved three key steps for the successful construction of the key tetrahydrofuran oxa-bridge skeleton, including a Wessely oxidative dearomatization, a novel intramolecular Diels-Alder reaction, and a Rh(II) -catalyzed O - H insertion reaction.

Keywords: Diels-Alder reaction; natural products; oxidative dearomatization; rhodium; total synthesis.