Experiments directed towards the synthesis of anthracyclinones. XIX. Elaboration of 2-formylquinizarin through a Wittig reaction

PJ Boniface, RC Cambie, DR Carroll, NF Marsh…

Index: Boniface, Peter J.; Cambie, Richard C.; Carroll, David R.; Marsh, Nicholas F.; Milbank, Jared B. J.; et al. Australian Journal of Chemistry, 1994 , vol. 47, # 3 p. 441 - 450

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Citation Number: 3

Abstract

Abstract Reaction of 2-formylquinizarin dimethyl ether (3) with the dimethoxy ylide (6) gives an α, β-unsaturated ester (8) which on hydrogenation, reduction and methylation gives the tetramethoxyanthracene diester (18). When linked to work by Dotz and Popall this sequence provides a route to (±)-4-demethoxydaunomycinone.