Novel approach for the introduction of a C-1 oxygenated group on the decalin skeleton: first asymmetric total synthesis of 1S,6S-dihydroxy-eudesm-3-ene.

This paper describes a novel approach for the introduction of a C-1 hydroxyl on the decalin ring system, starting from (-)-carvone. Utilizing the substratecontrolled Mukaiyama aldol reaction and alkaline cyclization as key steps, the C-1 oxygenated decalin eudesmane skeleton 2' and its four isomers were synthesized efficiently. Furthermore, X-ray structural analysis showed that the claimed structure for the natural product is incorrect. (C) 2004 Wiley-Liss, Inc.