Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

Experiments Directed Towards the Synthesis of Anthracyclinones. XXX. Formation and Use of an Anthraquinone Formyl Ester

RC Cambie, JBJ Milbank and PS Rutledge

Australian Journal of Chemistry 49(11) 1203 - 1215
Published: 1996


Methods for the preparation of methyl 3-formyl-1,4-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-acetate (1) from quinizarin (8) have been investigated. Reaction of the ester (1) with either a titanium enolate of acetone or with acetone trimethylsilyl enol ether and titanium tetrachloride gave the aldol (29) which was then converted into the pentacyclic lactone mixture (41) and (42). While hydrolysis of (41) and (42) with base for long periods (>30 min) gave α,β -unsaturated ketones , brief (2 min) treatment gave the dimethyl ether (5) of the 4-deoxyanthracyclinone (6) corresponding to the antitumour anthracycline 14A10.

© CSIRO 1996

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