Stereospecific total synthesis of 9-aminoanthracyclines:(+)-9-amino-9-deoxydaunomycin and related compounds

K Ishizumi, N Ohashi, N Tanno

Index: Ishizumi, Kikuo; Ohashi, Naohito; Tanno, Norihiko Journal of Organic Chemistry, 1987 , vol. 52, # 20 p. 4477 - 4485

Full Text: HTML

Citation Number: 83

Abstract

9-Amino-9-deoxydaunomycin and related compounds, in which the hydroxyl group at the 9- position of daunomycin is replaced by an amino group, have been synthesized. Asymmetry was introduced into the synthetic sequence for the AB synthon by resolution of the intermediate amino ester or acetamido acid to afford (R)-(--)-2-acetyl-2-acetamido-5, 8- dimethoxy-1, 2, 3, 4-tetrahydronaphthalene, which was converted to the tetracyclic amido ...