Highly stereocontrolled asymmetric syntheses of taxol and taxotere C-13 side chain analogues

Article abstract of DOI:10.1016/S0040-4020(01)81916-5

Asymmetric aldol reaction of (+)-tricarbonyl(η⁶-2-trimethylsilylbenzaldehyde)chromium(0) complex (4) with titanium enolate of S-tert-butyl benzyloxyethanethioate (10) provided, after consecutive desilylation and decomplexation, anti-aldol product 15 in a highly stereo selective manner. Anti-product 15 was subsequently converted to (2R,3S)-N-benzoyl- and N-tert-butoxycarbonyl-3-phenylisoserine methyl esters (23 and 24), C-13 side chain analogues of taxol (1) and taxotere (2).