Tetrahedron

A convergent synthesis of (+)-4-demethoxydaunomycinone and (+)-daunomycinone

JS Swenton, JN Freskos, GW Morrow, AD Sercel

Index: Swenton; Freskos; Morrow; Sercel Tetrahedron, 1984 , vol. 40, # 22 p. 4625 - 4632

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Citation Number: 39

Abstract

A convergent synthesis of (+)-4-demethoxydaunomycinone and (+)-daunomycinone via annelation of a functionalized quinone monoketal with the anion of the corresponding 3- cyano-l (3H) isobenzofuranone is reported. The quinone monoketal, sequence, was prepared without chromatography from 2, 5-dimethoxybenzaldehyde in sixteen steps. The monoketal of proper absolute configuration was obtained by resolution of the imine from ( ...