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

…, AA Shaik, S Azeeza, MS Malik, M Sandbhor

文献索引：Kamal, Ahmed; Shaik, Ahmad Ali; Azeeza, Shaik; Malik, M. Shaheer; Sandbhor, Mahendra Tetrahedron Asymmetry, 2006 , vol. 17, # 20 p. 2890 - 2895

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被引用次数: 13

摘要

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.