Ignacio Carrera, Margarita Brovetto, G. Seoane
Dec 15, 2013
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Journal
Tetrahedron-asymmetry
Abstract
Abstract A chemoenzymatic synthesis of an enantiopure 6-substituted 5,6-dihydro-2 H -pyran-2-one using bromobenzene as a starting material is presented. This important structural motif is found in a large number of chiral lactones that present a wide range of biological activities. The key features of the preparation include enzymatic dioxygenation of bromobenzene using Escherichia coli JM109 (pDTG601), microwave-assisted acyloin cleavage, and tin mediated lactonization. The stereochemical assignment for the alcohol was confirmed by NMR analysis of Mosheŕs derivatives.