Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Studies of Cycloheximide-Related Compounds. II. The Acid-catalyzed Condensation of Glutarimide-β-acetaldehyde with Ketones
Yoshiyuki EgawaSumio Umezawa
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1965 Volume 38 Issue 12 Pages 2169-2173

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Abstract

1) Glutarimide-β-acetaldehyde has been condensed with several aliphatic ketones by acidcatalysts to give mainly α,β-unsaturated ketoderivatives. The condensation with methyl iso-propyl ketone has given δ-(1, 1-dimethyl-2-oxo-n-propyl)-β-carbamoylmethyl-δ-valerolactone (III-1) and 3-(2-hydroxy-3,3-dimethyl-4-oxo-n-pentyl)-glutarimide (III-2). It has been found that the latter is an isomer of the product prepared by Nielsen’s aldol condensation procedure.
2) An analogous condensation with DL-2,4-dimethylcyclohexanone has given DL-anhydrocycloheximide and two stereoisomers of DL-gem-cycloheximide. The condensation with (2R:4R)-2, 4-dimethylcyclohexanone has given a similar result.
3) It has been shown that the acid-catalyzed hydration of anhydrocycloheximide affords α-epi-isocycloheximide.

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