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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 1, 1971 - Issue 3
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Original Articles

Synthesis of (3S,5R)-cis- and (3S,5S)-trans-3,5-Dimethylvalerolactones and Their Conversion to Biotransformation Products of (S)-5-Ethyl-5-(2′-pentyl)barbituric Acid

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Pages 169-174 | Received 28 Jun 1971, Published online: 03 Jan 2007

References

  • The generic name of this compound is penrobarbiral.
  • Cahn , R. S. , Ingold , C. K. and Pralog , V. 1956 . Experientia , 12 : 81 The Cahn, Ingold, and Prelog R and S designation of configuration is used in this paper
  • Maynert , E. W. and Dawson , J. M. 1952 . J. Blol. Chem. , 195 : 389
  • Palmer , K. R. , Fowler , M. S. , Wall , M. E. , Rhodes , L. S. , Waddall , W. J. and Baggert , B. 1969 . J. Pharmacol. Exp. Ther. , 170 : 355
  • Palmer , K. H. , Fowler , M. S. and Wall , M. E. 1970 . J. Pharmacol. Exp. Ther. , 175 : 38
  • Carroll , F. I. and Blackwell , J. T. 1970 . Chem. Comm. , 1616
  • 3-(2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl] glutarimide is an antibiotic substance isolated from Streomvcas arislus and is commonly called cycloheximida. The absoluta configuration of this compound has been determined (ref. 8 and 9)
  • Eisenbraun , E. J. , Osiecki , J. and Djerassi , C. 1958 . J. Amer. Chem. Soc. , 80 : 1261
  • Johnson , F. , Starkovsky , N. A. and Carlson , A. A. 1965 . J. Amer. Cham. Soc , 87 : 4612
  • Sondheimer , F. , Mechoulam , R. and Sprecher , M. 1964 . tetrahedron , 20 : 2473
  • Carroll , F. I. and Blackwell , J. T. 1970 . Tatrahedron Letters , 4173
  • Carroll , F. I. , Sobti , A. and Meck , R. 1971 . Tetrahedron Letters , 405
  • The names, metabolities 1(S), 2(S), 1(R), 2(R), 1(RS) and 2(RS) refer to the designation used by Palmer and co-workars (ref. 4 and 5)
  • In particular it will be possible to prepare the (ω-1)-hydroxy metabolites of the important barbiturates; (S)-5-ethyl-5-(2′-pentyl)-2-thiobarbiruric acid (thiopental), (S)-5-allyl-5-(2′-pentyl)barbituric acid (secobarbiral), and (S)-5-allyl-5-(2′-pentyl)-2-thiobarbituric acid (thiarylal)

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