Conversion of (-)-3-Dehydroshikimic Acid into Derivatives of the (+)-Enantiomer

Banwell, Martin; Edwards, Alison; Essers, Michael; Jolliffe, Katrina

Conversion of (-)-3-Dehydroshikimic Acid into Derivatives of the (+)-Enantiomer

Date

2003

Authors

Banwell, Martin

Edwards, Alison

Essers, Michael

Jolliffe, Katrina

Publisher

American Chemical Society

Abstract

(-)-3-DHS (1), a compound available in large quantity through "engineering" of the shikimic acid pathway, has been converted over eight steps into the methyl ester, ent-2, of the (+)-enantiomer. Methyl (+)-shikimate (15) and its C-3 epimer (ent-5) have also been prepared by related means.