A novel application of a Pd (0)-catalyzed nucleophilic substitution reaction to the regio-and stereoselective synthesis of lactam analogues of the epothilone natural …

…, JD DiMarco, CR Fairchild, JZ Gougoutas…

Index: Borzilleri; Zheng; Schmidt; Johnson; Kim; DiMarco; Fairchild; Gougoutas; Lee; Long; Vite Journal of the American Chemical Society, 2000 ,  vol. 122,  # 37  p. 8890 - 8897

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Citation Number: 132

Abstract

Several lactam analogues of the epothilones were prepared using a concise semisynthetic approach starting with the unprotected natural products. Highlighted in this strategy is a novel regio-and stereoselective Pd (0)-catalyzed azidation reaction of a macrocyclic lactone. Subsequent reduction and macrolactamization of the resulting azide acid intermediates provided the desired macrolactams in satisfactory overall yields. The entire three-step ...