Annelation reactions of quinone monoketals. Studies directed at an efficient synthesis of anthracyclinones

BL Chenard, MG Dolson, AD Sercel…

Index: Chenard, Bertrand L.; Dolson, Mark G.; Sercel, Anthony D.; Swenton, John S. Journal of Organic Chemistry, 1984 , vol. 49, # 2 p. 318 - 325

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Citation Number: 43

Abstract

The annelation chemistry of quinone monoketals with dimethyl homophthalate, 7-methoxy-3- (phenyl-sulfonyl)-l (3H)-isobenzofuranone, and 7-methoxy-3-cyano-1 (3H)- isobenzofuranone has been studied. The first two reagents mentioned above allowed the formation of oxygenated tri-and tetracyclic anthrone and anthraquinone systems in 4040% yields. While less extensively studied, the 7-methoxy-3-cyano-l (3H)-isobenzofuranone ...