Process for the synthesis of optically active anthracyclines

Details Process for the synthesis of optically active anthracyclines Process for the synthesis of optically active anthracyclines

C - Chemistry, Metallurgy

07

H

C07H 15/252 (2006.01) C07C 69/013 (2006.01) C07C 69/14 (2006.01)

Patent

CA 2429136

It is described a process for the synthesis of optically active anthracyclines of the formula (see formula I) wherein: R1 = H, OH, OCH3; R2 = H, OH; R3 = X, Y o Z where X = (see formula II) Y = (see formula III) Z = (see formula IV) characterized by the fact that the key intermediate (R)2-acetyl-2-hydroxy- 1,2,3,4-tetrahydronaphtalene 5,8-dialkoxy of the formula (see formula V) wherein: R = C1-3 alkyl, preferably methyl, is prepared from 5,8-dialocxy-3,4-dihydronaphtalene by acylation asymmetric dihydroxylation, transformation into chloroacetate, dehydrochloridation and final hydrolysis.

L'invention concerne un procédé pour la synthèse d'anthracyclines actives du point de vue optique, caractérisé en ce que l'intermédiaire clé (R)2-acétyle-2-hydroxy-1,2,3,4-tétrahydronaphtalène 5,8-dialcoxy est préparé à partir de 5,8-dialcoxy-3,4-dihydronaphtalène par acylation, dihydroxylation asymétrique, transformation en chloroacétate, déhydrochloridation, et hydrolyse finale.

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