Tetrahedron: Asymmetry

Baker's yeast-mediated approach to (−)-cis-and (+)-trans-Aerangis lactones

E Brenna, C Dei Negri, C Fuganti, S Serra

Index: Brenna, Elisabetta; Negri, Claudia Dei; Fuganti, Claudio; Serra, Stefano Tetrahedron Asymmetry, 2001 , vol. 12, # 13 p. 1871 - 1879

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Citation Number: 41

Abstract

The first enantioselective synthesis of natural (−)-cis-Aerangis lactone (−)-1a and its (+)-trans- diastereoisomer (+)-1b is described. The key steps in the synthesis are:(i) the enantiospecific and 100% diastereoselective baker's yeast reduction of 1, 4-keto acid 2, to afford enantiopure trans-cognac lactone (+)-10;(ii) the regioselective PPL-mediated hydrolysis of the primary acetate moiety of diacetate (+)-(3S, 4R)-3, obtained from (+)-10. ...