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