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

Banwell, MartinEdwards, AlisonEssers, MichaelJolliffe, Katrina2015-12-132015-12-130022-3263http://hdl.handle.net/1885/88395(-)-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.Keywords: Enantiomers; Chemical reactions; Derivatives; Esters; Organic acids; 3 dehydroshikimic acid; ester derivative; shikimic acid derivative; unclassified drug; article; enantiomer; reaction analysis; stereochemistry; synthesis; Indicators and Reagents; ShikimConversion of (-)-3-Dehydroshikimic Acid into Derivatives of the (+)-Enantiomer200310.1021/jo034689c2015-12-12