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Current Organocatalysis

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ISSN (Print): 2213-3372
ISSN (Online): 2213-3380

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Research Article

A Novel Baker’s Yeast-Mediated Microwave-Induced Reduction of Racemic 3-Keto-2-Azetidinones: Facile Entry to Optically Active Hydroxy β-Lactam Derivatives

Author(s): Aparna Das, Ram Naresh Yadav and Bimal Krishna Banik*

Volume 9, Issue 2, 2022

Published on: 24 February, 2022

Page: [195 - 198] Pages: 4

DOI: 10.2174/2213337209666220126123630

Price: $65

Abstract

Objective: Microwave technology, together with enzymatic catalysis, is a nature-friendly chemical synthesis method with low wastage of solvent and a good yield of the products.

Methods: Enzymes from various microorganisms can be used in the biochemical processes of a wide range of compounds assisted by microwave irradiation.

Results: In this work, the microwave-induced reaction of α-keto β-lactams by Baker's yeast in organic solvent was conducted to afford optically active cis and trans-α-hydroxy-β-lactams for the first time.

Conclusion: These hydroxy compounds are the precursors of numerous natural products of medicinal significance.

Keywords: Hydroxy β-lactams, optical activity, microwave, baker’s yeast, reduction, solvent.

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[1]
Suffness, M. Taxol: Science and Applications; CRC Press: Boca Raton, FL, 1995.
[2]
Ojima, I.; Habus, I.; Zhao, M.; Georg, G.I.; Jayasinghe, L.R. Efficient and practical asymmetric synthesis of the taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogs via chiral 3-hydroxy-4-aryl-.beta.-lactams through chiral ester enolate-imine cyclocondensation. J. Org. Chem., 1991, 56(5), 1681-1683.
[http://dx.doi.org/10.1021/jo00005a003]
[3]
Banik, B.K.; Manhas, M.S.; Bose, B.K. Enantiopure hydroxy β-lactams via glycosylation. Tetrahedron Lett., 1997, 38(29), 5077-5080.
[http://dx.doi.org/10.1016/S0040-4039(97)01130-1]
[4]
(a) Banik, B.K.; Bandyopadhyay, D. Advances in Microwave Chemistry. Taylor & Francis. CRC Press: UK and USA, 2019
(b) Yadav, R.N.; Banik, I.; Banik, B.K. Montmorillonite-catalyzed glysosylation of alcohols with glycals derived from galactose and glucose under microwave-induced reactions. J. Indian Chem. Soc., 2018, 95, 1385-1387.
(c) Mahato, A.; Sahoo, B.M.; Banik, B.K.; Mohanta, B.C. Microwave-assisted synthesis: Paradigm of green chemistry. J. Indian Chem. Soc., 2018, 95, 1327-1339.
[5]
Brieva, R.; Grich, J.A.; Sih, C.J. Chemoenzymic synthesis of the C-13 side chain of taxol: Optically active 3-hydroxy-4-phenyl. beta.-lactam derivatives. J. Org. Chem., 1993, 58(5), 1068-1075.
[http://dx.doi.org/10.1021/jo00057a018]
[6]
Forro, E.; Paal, T.; Tasnadi, G.; Fulop, F. A new route to enantiopure β-aryl-substituted β-amino acids and 4-aryl-substituted β-Lactams through lipase-catalyzed enantioselective ring cleavage of β-lactams. Adv. Synth. Catal., 2006, 348(7-8), 917-923.
[http://dx.doi.org/10.1002/adsc.200505434]
[7]
Qun, J.; Shanjing, Y.; Lehe, M. Tolerance of immobilized baker’s yeast in organic solvents. Enzyme Microb. Technol., 2002, 30(6), 721-725.
[http://dx.doi.org/10.1016/S0141-0229(02)00048-0]
[8]
Rotthaus, O.; Krüger, D.; Demuth, M.; Schaffner, K. Reductions of keto esters with baker’s yeast in organic solvents - a comparison with the results in water. Tetrahedron, 1997, 53(3), 935-938.
[http://dx.doi.org/10.1016/S0040-4020(96)01067-8]
[9]
Medson, C.; Smallridge, A.J.; Trewhella, M.A. The stereoselective preparation of β-hydroxy esters using a yeast reduction in an organic solvent. Tetrahedron Asymmetry, 1997, 8(7), 1049-1054.
[http://dx.doi.org/10.1016/S0957-4166(97)00050-5]
[10]
Johns, M.K.; Smallridge, A.J.; Trewhella, M.A. The use of liquefied petroleum gas (LPG) as a solvent for yeast reactions. Tetrahedron Lett., 2001, 42(25), 4261-4262.
[http://dx.doi.org/10.1016/S0040-4039(01)00664-5]
[11]
Wolfson, A.B.; Dlugy, C.; Shotland, Y. Glycerol as a green solvent for high product yields and selectivities. Environ. Chem. Lett., 2006, 5, 67-71.
[http://dx.doi.org/10.1007/s10311-006-0080-z]
[12]
Banik, I.; Becker, F.F.; Banik, B.K. Stereoselective synthesis of β-lactams with polyaromatic imines: Entry to new and novel anticancer agents. J. Med. Chem., 2003, 46(1), 12-15.
[http://dx.doi.org/10.1021/jm0255825] [PMID: 12502355]
[13]
Banik, B.K.; Becker, F.F.; Banik, I. Synthesis of anticancer β-lactams: mechanism of action. Bioorg. Med. Chem., 2004, 12(10), 2523-2528.
[http://dx.doi.org/10.1016/j.bmc.2004.03.033] [PMID: 15110834]
[14]
Banik, B.K.; Banik, I.; Becker, F.F. Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction. Bioorg. Med. Chem., 2005, 13(11), 3611-3622.
[http://dx.doi.org/10.1016/j.bmc.2005.03.044] [PMID: 15862989]
[15]
Das, A.; Banik, B.K. Microwave-assisted enzymatic reactions. Elsevier, 2021, 245-281.

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