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

Banwell, Martin G.; Edwards, Alison J.; Essers, Michael; Jolliffe, Katrina A.

doi:10.1021/jo034689c.s002

jo034689c_si_002.pdf (946.73 kB)

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

journal contribution

posted on 2003-07-30, 00:00 authored by Martin G. Banwell, Alison J. Edwards, Michael Essers, Katrina A. Jolliffe

(−)-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.