METHOD FOR PREPARING DERIVATIVES OF BACCATIN III Russian patent published in 2005 - IPC

FIELD: organic chemistry, chemical technology, medicine.

SUBSTANCE: invention relates to a novel method for preparing 14β-hydroxy-1,4-carbonate-desacetylbaccatin III and intermediate substances used in preparing new derivatives of taxane and possessing an antitumor activity. Method involves the following stages: a) protection of hydroxyls at positions 7 and 10 in 10-desacetylbaccatin III wherein R and R₁ are taken among hydrogen atom, (C₁-C₁₀)-alkyl or aryl, (C₁-C₁₀)-alkyl- or aryl-carbonyl, trichloroacetyl, (C₁-C₄)-trialkylsilyl; preferably, when R and R₁ are similar then they represent trichloroacetyl; when they are different then, preferably, R represents trichloroacetyl and R₁ represents acetyl; or R represents triethyl or trimethylsilyl and R₁ represents acetyl; b) two-stage oxidation to yield a derivative oxidized to carbonyl at position 13 and hydroxylated at position 14; c) carboxylation of vicinal hydroxyls at positions 1 and 14 to yield 1,14-carbonate derivative; d) reduction of carbonyl at position 13; e) removal of protective groups at positions 7 and 10. Also, invention relates to intermediate substances. Invention provides preparing intermediate substances used in synthesis of taxane.

EFFECT: improved preparing method.

8 cl, 8 ex