A novel approach for introduction of C-1 oxygenated group on decalin skeleton:: first asymmetric total synthesis of 1α,6α-dihydroxy-eudesm-3-ene

This paper describes a novel approach for introduction of C-1 hydroxy on decalin ring system starting from (-)-carvone. Utilizing the substrate controlled Mukaiyama aldol reaction and alkaline cyclization as key steps, the C-1 oxygenated decalin eudesmane skeleton 2' and its four isomers were synthesized efficiently. What's more, X-ray structural analysis confirmed sufficiently that something was wrong about the structure of natural product: 1beta,6beta-dihydroxy-7-epi-eudesm-3-ene as reported by the literature. (C) 2004 Elsevier Ltd. All rights reserved.