Chemoenzymatic and yeast-catalysed synthesis of diastereomeric ethyl γ-phenyl and γ-(n-pyridyl) paraconates

…, E Zangrando, P Buzzini, M Goretti, B Turchetti

Index: Forzato, Cristina; Furlan, Giada; Nitti, Patrizia; Pitacco, Giuliana; Valentin, Ennio; Zangrando, Ennio; Buzzini, Pietro; Goretti, Marta; Turchetti, Benedetta Tetrahedron Asymmetry, 2008 , vol. 19, # 17 p. 2026 - 2036

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Citation Number: 8

Abstract

The synthesis of γ-phenyl and γ-(n-pyridyl) paraconates was accomplished by chemical reduction of their respective ketodiester precursors followed by cyclisation of the resulting hydroxy diester intermediates. The cis-and trans-lactones thus obtained were separated and separately subjected to enzymatic hydrolysis with HLAP. The cis-lactonic esters had enantiomeric excesses ranging from 94% to 99%, while for the trans-isomers the ee's ...