Total synthesis of 11-deoxyanthracyclines: 4-Demethoxy-11-deoxydaunomycin, 11-deoxydaunomycin, and their analogues.

Y TAMuRA, S AKAI, H KISHIMOTO, M SASHO…

Index: Tamura; Akai; Kishimoto; Sasho; Kirihara; Kita Chemical and Pharmaceutical Bulletin, 1988 ,  vol. 36,  # 10  p. 3897 - 3914

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Citation Number: 17

Abstract

Practical total synthesis of 11-deoxyanthracyclinones (8 and 9) was accomplished on the basis of two effective syntheses of the key intermediates (14 and 15) and the subsequent highly stereoselective introduction of a C-7 cis-hydroxyl group. Glycosidation of 8 with a suitably protected L-daunosamine (37) followed by deprotection provided 4-demethoxy-11- deoxydaunomycin (5). The C-13 acetal derivative (34) of 9 was successfully employed for ...