A practical synthesis of enantiopure (R)-4-hydroxy-2-cyclohexen-1-one

Article abstract of DOI:10.1002/jlac.199619961010

The title compound R-4a was prepared from (-)-quinic acid (1) in 6 steps in 18% overall yield (Scheme 3) and with 100% enantiomeric purity (Figure 1). The initiating step is the regio- and stereoselective acetalization of the trans-oriented vicinal OH groups of 1 (+ 5 → 8). Alcohol A-4a can be protected as the 2-ethoxyethyl ether A-4e (78%). VCH Verlagsgesellschaft mbH, 1996.