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Synthesis 1995; 1995(2): 181-186
DOI: 10.1055/s-1995-3882
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Synthesis of Taxol and Taxotere Side Chains by 2-(Trimethylsilyl)thiazole Based Homologation of L-Phenylglycine

Alessandro Dondoni* , Daniela Perrone, Teresa Semola
  • *Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, I-44100 Ferrara, Italy
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Publication History

Publication Date:
31 December 2000 (online)

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L-Phenylglycine is homologated by the use of 2-(trimethylsilyl)thiazole into (2R,3S)-N-benzoyl- and N-tert-butoxycarbonyl-3-phenyl-isoserine, which are isolated as acetonide derivatives in 47 and 35% overall yields and with 84 and 90% ee, respectively.

L-phenylglycinal - 3-phenylisoserine - taxol - taxotere - 2-(trimethylsilyl)thiazole - homologation - stereocontrolled addition