Highly stereocontrolled asymmetric syntheses of taxol and taxotère C-13 side chain analogues
1993; Elsevier BV; Volume: 49; Issue: 37 Linguagem: Inglês
10.1016/s0040-4020(01)81916-5
ISSN1464-5416
AutoresChisato Mukai, In Jong Kim, Etsuko Furu, Miyoji Hanaoka,
Tópico(s)Microbial Natural Products and Biosynthesis
ResumoAsymmetric 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 stereoselective 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 taxotère (2).
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