Beilstein J. Org. Chem.2020,16, 616–620, doi:10.3762/bjoc.16.57
Adam Drop Hubert Wojtasek Bozena Frackowiak-Wojtasek Institute of Chemistry, Opole University, ul. Oleska 48, 45-052 Opole, Poland ZWP EMITOR S.C., ul. Olimpijska 6, 45-681 Opole, Poland 10.3762/bjoc.16.57 Abstract 2,3-Butanediacetal derivatives were used for the stereoselective synthesis of
-5,6-dimethyl-1,4-dioxane-2-carboxylate as the starting material.
Keywords: 2,3-butanediacetal; cis-epoxide; (−)-disparlure; (+)-disparlure; (−)-monachalure; (+)-monachalure; Introduction
Compounds containing chiral epoxides display a wide range of biological activities and a number of them are
have been described [26][30][31] and we decided to prepare them starting from 2,3-butanediacetal derivatives of ʟ-tartaric acid. This method uses cheap and easily available starting materials, does not require expensive chiral catalysts and offers the possibility of obtaining both enantiomers of
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Graphical Abstract
Scheme 1:
Retrosynthesis of (+)-disparlure (1), (−)-disparlure (3), (+)-monachalure (2), and (−)-monachalure (...