Asymmetric synthesis of (-)-steganone. Further application of chiral biaryl syntheses

AI Meyers, JR Flisak, RA Aitken

Index: Meyers,A.I.; Flisak,J.R.; Aitken,R.A. Journal of the American Chemical Society, 1987 , vol. 109, p. 5446

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Citation Number: 144

Abstract

Abstract: An asymmetric synthesis of the title compound has been achieved by initially forming an axially chiral biphenyl precursor lla mediated by a chiral aromatic oxazoline (+)- lo. The eight-membered ring was constructed around the biphenyl with particular attention addressing the rotational barrier for biphenyls to avoid racemization. The efficiency of this total synthesis was quite good until the last step, which incorporates the lactone moiety. ...