Tetrahedron

5-Methoxy-pentono-1, 4-lactones from (R)-2-hydroxy-5-methoxy-3-pentenoic acid obtained by bioreduction of the 2-oxo acid

D Bonnaffé, H Simon

Index: Bonnaffe, David; Simon, Helmut Tetrahedron, 1992 , vol. 48, # 44 p. 9695 - 9706

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Citation Number: 14

Abstract

Various 5-methoxy-pentono-1, 4-lactones and derivatives thereof were synthesised from propargyl alcohol or its methyl ether. The key step was the enantioselective reduction of 2- oxo-5-alkoxy-3-pentenoic acids by resting cells of Proteus vulgaris. The (R)-2-hydroxy-5- methoxy-3-pentenoic acid (ee.> 96%) was further functionalized via epoxidation, or hydroxylation with osmium tetroxide, or bromine addition, with modest to good ...