Glutarimide antibiotics part VI. The nature of deoxycycloheximide and epideoxycycloheximide

Glutarimide Antibiotics. VII. The Synthesis of dl-Neocycloheximide and the Determination of the Cyclohexanone Ring Stereochemistry of Cycloheximide, Its Isomers,1 and Inactone

“…That the methyl groups in I are trans oriented was also shown quite independently by Schaeffer and Jain20 although the evidence which formed the basis for this conclusion is now in doubt. 21 Subsequently, in a refined analysis of the optical rotatory dispersion data, Okuda and Suzuki22 concluded that cycloheximide has structure Ie rather than Ic. The Japanese workers have followed this up by applying Lawes' pyrolysis procedure to naramycin-B and isocycloheximide.23 As expected, the former affords (ran5-2,4-dimethylcyclohexanone and the latter yields the corresponding cis isomer.…”