A highly enantioselective chemoenzymatic synthesis of syn-3-amino-2-hydroxy esters: key intermediates for taxol side chain and phenylnorstatine |
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| Institution: | 1. Department of Physiology, College of Medicine, University of Kentucky Medical Center, Lexington, Kentucky;2. Department of Pharmacology and Nutritional Science, College of Medicine, University of Kentucky Medical Center, Lexington, Kentucky;1. Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, Sienkiewicza 112 90-363 Łódź, Poland;2. Department of Organic and Applied Chemistry, University of Łódź, Tamka 12 91-403 Łódź, Poland;1. Dr. Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500046, India;2. Chemistry Division, Institute of Science and Technology, JNT University, Kukatpally, Hyderabad 500072, India;3. The University of Queensland, School of Pharmacy, Brisbane, QLD 4072, Australia;4. Department of Chemistry, Acharya Nagarjuna University, Guntur 522510, Andhra Pradesh, India |
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| Abstract: | 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. |
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