Such (+)- and (-)-cw-cycloheximide isomers as isocycloheximide (
la,
lb), a-epiisocycloheximide (
2a,
2b) and neocycloheximide (
3a,
3b) were synthesized by aldol condensation of (-)-(2R, 4R)- and (+)-(2S, 4S)-
cis-2, 4-dimethyl-l-cyclohexanone (
5a,
5b), obtained by microbial resolution, with 4-(2-oxoethyl)-2, 6-piperidinedione (
7). The absolute configuration of the ( - )-cisketone
5a was confirmed by chemical correlation with natural (2S, 4S, 6S, αR-cycloheximide (
4). The newly synthesized isomer, (-)-α-epiisocycloheximide (
2b), showed strong antimicrobial activity against
S. cerevisiae and
P. oryzae close to that of natural cycloheximide (
4).
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