Asymmetric 9-hydroxylation of anthracyclinones. Total synthesis of (+)-4-demethoxydaunomycinone

D Dominguez, MP Cava

Index: Dominguez, Domingo; Cava, Michael P. Journal of Organic Chemistry, 1983 , vol. 48, # 17 p. 2820 - 2825

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Citation Number: 26

Abstract

3, R,= R,= R,= H; R,= OH 4, R,= OMe; R,= R,= R,= H 5, R,= OH; R,= R,= R,= H 6, R,= R,= R,= R,= H 7, R,= R,= R,= H; R,= Me 8, R,= R,= H; R,= R,= OH obtained either by resolution of racemic material3 or by asymmetric~ ynthesis.~ The chiral bicyclic compound is then transformed into a tetracyclic intermediate, Le., 3, by using Wong's synthetic sequence? a reaction that suffers from a lack of regiochemical control, leading to a difficult separation of ...