A short and efficient synthesis of (+)-totarol

Abstract

A concise route to multigram quantities of the antibacterial diterpene (+)-totarol (1) is reported. (-)-Sclareol (2) was converted to the target compound 1 using either a six- or a seven-step sequence, while only three steps were required to access (+)-totarol ( 1) starting from (+)-manool (9) or (+)-13-epi-manool (10), respectively. A novel one-pot intramolecular aldol condensation/α-alkylation protocol served as the key operation for streamlining the syntheses of 1. ©ARKAT-USA, Inc.