Highly diastereoselective formation of spirocyclic compounds via 1,5-hydrogen transfer: A total synthesis of (-)-erythrodiene

Article abstract of DOI:10.1021/ol051426r

(Chemical Equation Presented) A highly stereoselective synthesis of (-)-erythrodiene starting from 4-isopropylcyclohexanone is described. The key reactions are an asymmetric methoxycarbonylation of the starting ketone and a highly diastereoselective radical cascade involving addition of a phenylthiyl radical to a terminal alkyne followed by a 1,5-hydrogen transfer and a 5-exo-cyclization.