Regio-and stereospecific construction of anthracyclinones: total syntheses of (.+-.)-. gamma.-citromycinone,(.+-.)-dimethyl-6-deoxydaunomycinone, and (.+-.)-dimethyl- …

FM Hauser, P Hewawasam, D Mal

Index: Hauser; Hewawasam; Mal Journal of the American Chemical Society, 1988 , vol. 110, # 9 p. 2919 - 2924

Full Text: HTML

Citation Number: 2

Abstract

Abstract: Total syntheses of (h)-y-citromycinone (1) and of the dimethyl ether derivatives of (3=)-6-deoxydaunomycinone (29) and (*)-6-deoxyadriamycinone (2b) are described. Key elements of these preparations were regiospecific construction of the anthraquinone 15 through condensation of the (phenylsulfony1) isobenzofuranone 12 with the cyclohexenone 13, ene cyclization of the anthraquinone aldehyde 17c to the naphthacenone 18, and use ...