Asymmetric synthesis of (-)-trichodiene. Generation of vicinal stereogenic quaternary centers via the thio-Claisen rearrangement

RM Lemieux, AI Meyers

Index: Lemieux, Rene M.; Meyers Journal of the American Chemical Society, 1998 , vol. 120, # 22 p. 5453 - 5457

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Citation Number: 55

Abstract

The use of chiral bicyclic lactams, in their thiocarbonyl form 9, has been shown to serve as important intermediates for producing α-quaternary alkyl derivatives 8, which were readily transformed into the title compound (-)-1. The reversibility of the thio-Claisen rearrangement, 15⇌ 8, was clearly demonstrated and appears to be unprecedented. Solvent effects to alter the equilibrium position were studied and found to have only a moderate, but beneficial ...