Patent ID: 6603023
Filing Date: 2003-08-05
Classification: A61K,C07C,C07D,C07F

Abstract:
A method of preparing a desoxyepothilone having the structure: wherein R, R0 and Râ€² are independently H, linear or branched chain alkyl, optionally substituted by hydroxy, alkoxy, carboxy carboxaldedyde, linear or branched alkyl or cyclic acetal, fluorine, NR1R2, N-hydroximino, or N-alkoxyimino, wherein R1 and R2 are independently H, phenyl, benzyl, linear or branched chain alkyl; wherein Râ€³ is â€”CY&boxH;CHX, or H, linear or branched chain alkyl, phenyl, 2-methyl-1,3-thiazolinyl, 2-furanyl, 3-furanyl, 4-furanyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, imidazolyl, 2-methyl-1,3-oxazolinyl, 3-indolyl or 6-indolyl; wherein X is H, linear or branched chain alkyl, phenyl, 2-methyl-1,3-thiazolyl, 2-furanyl, 3-furanyl, 4-furanyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, imidazolyl, 2-methyl-1,3-oxazolyl, 3-indolyl or 6-indolyl; wherein Y is H or linear or branched chain alkyl; and wherein Z or O, N(OR3) or Nâ€”NR4R5 where R3, R4 and R5 are independently H or a linear or branched alkyl; and wherein n is 0, 1, 2, or 3; which comprises treating a protected desoxyepothilone having the structure: wherein RA is a linear or branched alkyl, alkoxyalkyl, substituted or unsubstituted aryloxyalkyl, trialkylsilyl, aryldialkylsilyl, diarylalkylsisyl, triarylsilyl, linear or branched acyl, substituted or unsubstituted aroyl or benzoyl; and wherein RB is hydrogen, t-butyloxycarbonyl; amyloxycarbonyl, (trialkylsilyl)alkyloxycarbonyl, (dialkylarylsilyl)alkyloxycarbonyl, benzyl, trialkylsilyl, dialkylarylsilyl, alkyldiarylsilyl, triarylsilyl, a linear or branched acyl, substituted or unsubstituted aroyl or benzoyl; under suitable conditions to form the desoxyepothilone.