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Chemoenzymatic synthesis of (5S)- and (5R)-hydroxymethyl-3,5-dimethyl-4-(methoxymethoxy)-5H-thiophen-2-one: a precursor of thiolactomycin and determination of its absolute configuration
Journal article   Peer reviewed

Chemoenzymatic synthesis of (5S)- and (5R)-hydroxymethyl-3,5-dimethyl-4-(methoxymethoxy)-5H-thiophen-2-one: a precursor of thiolactomycin and determination of its absolute configuration

Ahmed Kamal, Ahmad Ali Shaik, Shaik Azeeza, M. Shaheer Malik and Mahendra Sandbhor
Tetrahedron: asymmetry, Vol.17(20), pp.2890-2895
06/11/2006
DOI: https://doi.org/10.1016/j.tetasy.2006.10.032

Abstract

Chemistry Chemistry, Inorganic & Nuclear Chemistry, Organic Chemistry, Physical Physical Sciences Science & Technology
A convenient enantioselective synthesis of (5S)- and (5R)-hydroxymethyl-3,5-dimethyl-4-(methoxymethoxy)-5H-thiophen-2-one, a key intermediate in the synthesis of thiolactomycin has been carried out by a Carica papaya lipase-mediated resolution protocol to provide (R)-2 in a 94% ee and its enantiomer (S)-9 in a 98% ee. The absolute configuration at the C-5 position has been determined by Mosher's method. (c) 2006 Elsevier Ltd. All rights reserved.

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