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 and its four isomers were synthesized efficiently. Whatʹs more, X-ray structural analysis confirmed sufficiently that something was wrong about the structure of natural product: 1β,6β-dihydroxy-7-epi-eudesm-3-ene as reported by the literature.