Enantioconvergent synthesis of (-)-(S)- and (+)-(R)-2-acetyl-3,6-dihydroxycyclohex-2-enone starting from rac-6-hydroxy-3-methoxycyclohex-2-enone.
The synthesis of enantiomerically pure (-)-(S)- and (+)-(R)-2-acyl-3,6-dihydroxycyclohex-2-enone starting from diastereomerically pure N-tosyl-(S)-proline esters 3-methoxy-6-hydroxycyclohex-2-enone 1 is presented. An enantioconvergent synthesis of either (-)-(S)- and (+)-(R)-2-acyl-3,6-dihydroxycyclohex-2-enone starting with the racemic alpha-ketol 1 through a conversion of ( approximately 1:1) mixture of diastereomeric esters into one diastereomer by a repeated crystallization, followed by dimethylaminopyridine-catalyzed equilibration as key steps is described.
Zaitsev
V G
VG
Institute of Bio-Organic Chemistry, National Academy of Science of Belarus, 5/2 Kuprevicha Str., 220141 Minsk, Belarus. vgzaitsev@yahoo.vom
Mikhal'chuk
A L
AL
D003511:Cyclohexanols / Q000138:chemical synthesis / Q000737:chemistry; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D007301:Insect Hormones / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry
C435706:2-acetyl-3,6-dihydroxycyclohex-2-enone; C435707:6-(N-tosylprolyloxy)-3-methoxycyclohex-2-enone; D003511:Cyclohexanols; D003512:Cyclohexanones; D007301:Insect Hormones; D014105:Tosyl Compounds; C013078:kairmones