A concise, enantioselective approach to (-)-quinic acid.
[reaction: see text] An expedient, enantioselective synthesis of a key precursor to (-)-quinic acid has been achieved from an ephedrine-derived morpholine-dione. The salient features of this approach are a highly diastereoselective conversion of the dione to a dialkenyl morpholinone and a subsequent ring-closing metathesis reaction. Removal of the ephedrine portion generates an enantiomerically enriched hydroxycyclohexene carboxamide that is readily converted to the quinic acid precursor.
Pansare
Sunil V
SV
Department of Chemistry, Memorial University of Newfoundland, St. John's, Canada. spansare@mun.ca
Adsool
Vikrant A
VA