Synthesis and Antimicrobial Activity of Optically Active trans-Cycloheximide Isomers |
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Authors: | Sachio Kudo Takayuki Oritani Kyohei Yamashita |
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Institution: | Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University, Sendai 980, Japan |
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Abstract: | Optically active tiraras-cycloheximide isomers such as cycloheximide (2S,4S,6R,αR)-form (1)], naramycin B(25,4S,6RαR)-form(4)], and new stereoisomers (2S,4S,6S,αS)-form (8) and (2S,4S,6R,αS)-from (9) were synthesized by an aldol condensation of trans-2,4-dimethyl-l-cyclohexanone (5b), with 4-(2-oxoethyl)-2,6-piperidinedione(6). The antimicrobial activity of trans- cycloheximide isomers (1, 4, 8, and 9) was examined against S. cerevisiae and P. oryzae. The stereoisomers 1 and 4 exhibited marked antimicrobial activity against both microorganisms as compared with their C- α-epimers 8 and 9. |
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