Helvetica chimica acta

Practical Enzymatic Desymmetrization of 2??(Ethoxycarbonyl) propane??1, 3??diyl Dihexanoate and Model Cyclization for the A–D Ring System of Lysergic Acid

S Miyata, T Kumamoto, T Ishikawa

Index: Miyata, Sachiho; Kumamoto, Takuya; Ishikawa, Tsutomu Helvetica Chimica Acta, 2007 , vol. 90, # 7 p. 1420 - 1438

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Citation Number: 3

Abstract

Abstract Porcine pancreas lipase-catalyzed hydrolysis of symmetrical 2-(ethoxycarbonyl) propane-1, 3-diyl dihexanoate, under the modified conditions of the Seebach protocol, afforded a desymmetrized monohexanoate in 40–51% yield with 91–94% ee, even in a gram-scale reaction. The absolute configuration of a half-hydrolyzed (−)-product was determined to be (R) by conversion to a known 2-methylpropane-1, 3-diol derivative. ...