One-pot Eschenmoser episulfide contractions in DMSO: Applications to the synthesis of fuligocandins A and B and a number of vinylogous amides

B Pettersson, V Hasimbegovic…

Index: Pettersson, Birgitta; Hasimbegovic, Vedran; Bergman, Jan Journal of Organic Chemistry, 2011 , vol. 76, # 6 p. 1554 - 1561

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Citation Number: 27

Abstract

Practical total syntheses of the natural products fuligocandin A (2a) and fuligocandin B (3) have been achieved through a convergent strategy depending on the Eschenmoser episulfide contraction as a key step. Conducting the reaction in DMSO proved to be an efficient and general method for the synthesis of a variety of vinylogous amides, such as azepan-2-ylidenepropan-2-one.