Synthesis and Antimicrobial Activity of Chiralcis-Cycloheximide Isomers

Synthesis of Streptovitacin-C2Isomers

“…C-cxsignals of the isomers (17a, l7b, la and lb) were good indicators for the determination of relative stereochemistry between C-6 and C-cx. In our previous reports, 3,4) it was revealed that the C-cx methyl signals of the threo isomers From these data (Table I), (±)-17a, (-)-17b and (± )-la were concluded to be the threo form, and also ( +)-lb to be the erythro form.…”

“…1H -NMR data also supported this conclusion, the signals of the C-cx-proton of (± )-17a, ( -)-17b and (± )-la showing the multiplet characteristic of such threo isomers as isocycloheximide (12)4) or naramycin B (13),3) and that of (+ )-lb showing d-d-d coupling (10.7, 2.4, 2.4 HZ)7) that is characteristic of such erythro isomers as cycloheximide (4).…”

“…In this paper, we report the synthesis and STV-C 2 (1), STV-B (2) and STV-A (3),1) the hydroxylated analogs of cycloheximide (4), are known as antitumor agents isolated from the cultured broth of Streptomyces griseus. Their chemical structures (Fig.…”

Notes on the directed aldol synthesis and reduction of some compounds related to cycloheximide

“…Nonetheless, the preferential formation of some isomers might ensue (2) when steric hindrance is encountered between the trimethylsiloxy group of the cyclohexene and a substituent at position 6. Kudo et al (3,4), for example, found a favored isomer to prevail in their work on 4,6-dimethyl-1 -trimethylsiloxycyclohexenes. Stereochemical identification of the isolated compounds was established through 'H nmr data for the carbinol proton and for the cyclohexane ring methyl groups.…”

“…We began by examining the TiC14-promoted directed aldol condensation procedure, initially described by T. Mukaiyama et al (2), to develop an efficient strategy for the synthesis of additional analogues whereby the cyclohexane ring substituents and (or) the imide ring portion of the molecule could be varied before introducing the P-hydroxyketone system. Recently, S. Kudo et al (3,4) used titanium and tin halide mediated methods to prepare optically active tratzs-cycloheximide isomers and chiral cis-cycloheximide isomers for antimicrobial activity studies. Thus, the method offered promise.…”