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Journal of the American Chemical Society

A total synthesis of anthramycin. Application of palladium-catalyzed coupling reactions for the attachment of the acrylic side chain

MR Pena, JK Stille

文献索引:Pena; Stille Journal of the American Chemical Society, 1989 , vol. 111, # 14 p. 5417 - 5424

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被引用次数: 57

摘要

Abstract: Utilization of the palladium-catalyzed reactions of vinyl triflates 8 obtained from model N-substituted (1 1aS)-2, 3, 5, 10, 11, 1 la-hexahydro-2, 5, 1 l-trioxo-1H-pyrrolo [2, 1- c][1, 4] benzodiazepines (5, 6) either with 0-(tributylstanny1) acrylates or acrylic esters and amides yields coupled products (9-13) having the basic anthramycin framework. Generation of the enol triflates from the 2-keto precursors is regiospecific, introducing the double bond ...