title: Conversion of (-)-3-dehydroshikimic acid into derivatives of the (+)-enantiomer.
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.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. mgb@rsc.anu.edu.au
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.forename: Alison J
authors.initials: AJ
authors.lastname: Edwards
authors.forename: Michael
authors.initials: M
authors.lastname: Essers
authors.forename: Katrina A
authors.initials: KA
authors.lastname: Jolliffe
mesh_terms: D007202:Indicators and Reagents; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007202:Indicators and Reagents; C096387:3-dehydroshikimate; D012765:Shikimic Acid