
TY  - JOUR
A1  - Cambie, RC 
A1  - Milbank, JBJ 
A1  - Rutledge, PS 
T1  - Experiments Directed Towards the Synthesis of Anthracyclinones. XXX. Formation and Use of an Anthraquinone Formyl Ester
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1996
VL  - 49
IS  - 11
SP  - 1203
EP  - 1215
KW  - 
UR  - https://doi.org/10.1071/CH9961203 
N2  - 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 &#945;,&#946; -unsaturated ketones , brief (2 min) treatment gave the dimethyl ether (5) of the 4-deoxyanthracyclinone (6) corresponding to the antitumour  anthracycline 14A10. 
ER  -

