Enantiodivergent, Biocatalytic Routes to Both Taxol Side Chain Antipodes
Document Type
Article
Publication Date
11-13-2005
Publication Title
Journal of Organic Chemistry
DOI
10.1021/jo0516077
ISSN
1520-6904
Abstract
Two enantiocomplementary bakers' yeast enzymes reduced an alpha-chloro-beta-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 converted directly to the oxazoline form of the target molecules using a Ritter reaction with benzonitrile. These were hydrolyzed to the ethyl ester form of the Taxol side chain enantiomers under acidic conditions. This brief and atom-efficient route to both target enantiomers demonstrates both the synthetic utility of individual yeast reductases and the power of genomic strategies in making these catalysts available.
Recommended Citation
Feske, Brent D., Iwona A. Kaluzna, Jon D. Stewart.
2005.
"Enantiodivergent, Biocatalytic Routes to Both Taxol Side Chain Antipodes."
Journal of Organic Chemistry, 70 (23): 9654-9657: ACS Publications.
doi: 10.1021/jo0516077 source: https://pubs.acs.org/doi/10.1021/jo0516077
https://digitalcommons.georgiasouthern.edu/chem-facpubs/135
