PURPOSE: To produce the titled compound useful as a synthetic intermediate of a compound having carcinostatic activity, with simple reaction operation, in high yield, by reacting a specific carboxylic acid derivative with a specific carbonyl compound, and reacting the reaction product with a Grignard reagent.
CONSTITUTION: The objective compound of formula IV useful as a synthetic intermediate of the compound of formula III (X is R) which is an aglicon of a non-natural anthracycline exhibiting excellent carcinostatic activity, is produced by (1) reacting the 2, 5-dihydroxy-1,2,3,4-tetrahydronaphthacene-6,11-dione-2- carb-oxylic acid derivative of formula I (R is H or OH) with the carbonyl compound of formula II (A and A' are azole group) such as 1,1'- carbonyldiimidazole, etc. in a solvent, and (2) reacting the obtained reaction mixture with a Grignard reagent of formula R1MgX (R1 is alkyl, aralkyl or aryl; X is halogen) in the presence of a Lewis acid. When an optically active compound is used as the raw material, it can be converted to the optically active compound having the corresponding absolute configuration without causing the racemization.
KIMURA YOSHIICHI
MATSUMOTO MITSUYO
SUZUKI MICHIYO
ABE RUMIKO