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

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
12
Issue
13
Identifiers
DOI: 10.1016/s0957-4166(01)00314-7

Abstract

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 (+)-(3 S,4 R)- 3, obtained from (+)- 10. Chain elongation by one carbon atom via cyanide substitution, and inversion of the configuration of C(5) in nitrile derivative (+)- 21a are also required to complete the synthetic route to (−)- 1a.

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