Total syntheses of (-)-herbertenediol,(-)-mastigophorene A, and (-)-mastigophorene B. Combined utility of chiral bicyclic lactams and chiral aryl oxazolines

AP Degnan, AI Meyers

Index: Degnan, Andrew P.; Meyers Journal of the American Chemical Society, 1999 , vol. 121, # 12 p. 2762 - 2769

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Citation Number: 91

Abstract

A nonracemic bicyclic lactam has been used to construct a chiral cyclopentane containing vicinal quaternary carbon centers in optically pure form, which is common to all of the title compounds. An oxazoline-mediated asymmetric Ullmann coupling was then utilized to establish chirality about the biaryl axis of mastigophorenes A and B. Through the course of this synthesis, it was clearly demonstrated that smaller chiral auxiliaries lead to higher ...