Seikou Kimura, Ryoko Ehama, K. Inomata
Jun 1, 2002
Citations
0
Influential Citations
5
Citations
Journal
Synthesis
Abstract
Optically pure C 2 -symmetric 4-cyclopentene-1,3-diol has been prepared in both enantiomeric forms from racemic (3aS * ,4R * ,7S * ,7aS * )-3a,4,7,7a-tetrahydro-4,7-methano-1H-inden1-one by employing lipase-mediated kinetic resolution as the key step. As a result, the known (3aS * ,4R * ,7S * ,7aS * )-3a,4,7,7a-tetrahydro-4,7-methano-1H-inden-1-one is transformed into (1'S * ,3'S * ,3'aR * ,4'S * ,7'R * ,7'aS * )- 2',3',3'a,4',7',7'a-hexahydro-3'-hydroxy-4',7'-methano-1'H-inden-1'-yl benzoate, via stereo- and regioselective hydride reduction of epoxy ketone and sequential benzoylation, which is resolved under transesterification conditions in the presence of lipase. The hydride reduction of benzoate and acetate gives the corresponding chiral diols, which are further transformed into both enantiomers of C 2 -symmetric 4-cyclopentene-1,3-diol via a retro-Diels-Alder reaction.