869012-73-7Relevant academic research and scientific papers
A highly enantioselective chemoenzymatic synthesis of syn-3-amino-2-hydroxy esters: Key intermediates for taxol side chain and phenylnorstatine
Rodrigues, J. Augusto R.,Milagre, Humberto M. S.,Milagre, Cintia D. F.,Moran, Paulo J. S.
, p. 3099 - 3106 (2007/10/03)
Starting from the bromination of α-ketoesters to obtain 3-bromo-2-oxoalkanoates and bioreduction with Saccharomyces cerevisiae entrapped in calcium alginate pellets with double gel layers, syn-(2R,3S)-β-bromo- α-hydroxy esters were obtained regioselectively in high yields and high ee. These chiral bromohydrins were cyclized to epoxides that were transformed into oxazolidines and finally opened by acidic hydrolysis to give syn-(2S,3S)-β-amino-α-hydroxy esters in high overall yields and high ee. The enantiomeric excesses of all the intermediates were maintained during the reaction sequence.
Enantiodivergent, biocatalytic routes to both taxol side chain antipodes
Feske, Brent D.,Kaluzna, Iwona A.,Stewart, Jon D.
, p. 9654 - 9657 (2007/10/03)
Two enantiocomplementary bakers' yeast enzymes reduced an α-chloro-β-keto ester to yield precursors for both enantiomers of the N-benzoyl phenylisoserine Taxol side chain. After base-mediated ring closure of the chlorohydrin enantiomers, the epoxides were
