Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 8, 1978 - Issue 2
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Original Articles

An Improved Synthesis of la, 3 p-Dihydroxycholesta- 5,7-Diene

Pages 127-134 | Received 21 Nov 1977, Published online: 05 Dec 2006

References

  • After October, 1977, all correspondence should be addressed to A. Mouriño, Departamento de Quimica Organica, Facultad de Ciencias, Santiago de Compostela, Spain
  • Haussler , M. R. , Zerwekh , J. E. , Hesse , R. H. , Rizzardo , E. and Pechet , M. 1973 . Proc. Acad. Sci., (U. S.) , 70 : 2248
  • Barton , D. H. R. , Hesse , R. H. , Pechet , M. and Rizzardo , E. J. 1973 . J. Amer. Chem. Soc. , 95 : 2748
  • Harrison , R. G. , Lythgoe , B. and Wright , P. W. 1973 . Tetrahderon Letters , : 3649
  • Furst , A. , Labler , L. , Meier , W. and Pfoertner , K. H. 1973 . Helv. Chim. Acta , : 1708
  • Holick , M. F. , Semmler , E. , Schoes , H. K. and DeLuca , H. F. 1973 . Science , 180 : 190
  • Brickman , A. S. , Coburn , J. W. and Norman , A. W. 1972 . New Eng. J. Med. , 287 : 891
  • Omdahl , J. L. , Gray , R. W. , Boyle , I. T. , Knutsen , J. and DeLuca , H. F. 1971 . Nature (London) , 237 : 63 A. W. Norman and R. J. Wing, J. Nutr., 102, 1709 (1972)
  • Okamura , W. H. , Mitra , M. N. , Wing , R. M. and Norman , A. W. 1974 . Biochem. Biophys. Res. Commun. , 60 : 179
  • Mitra , M. N. , Norman , A. W. and Okamura , W. H. 1974 . J. Org. Chem. , 39 : 2931
  • Hesse , R. H. , Rizzardo , E. and Barton , D. H. R. U. S. Patent . 3, 901, 928 . 1975 .
  • Crystallization of the diacetate 3b afforded material with m. p. 98–9°C. Lit10 : liquid
  • The purified products by column chromatography showed consistant data (TLC, UV, NMR) with pure materials
  • The efficiency of the bromination and dehydrobromination method may be observed in the following experiment: bromination and dehydrobromination of cholesteryl acetate (200 mg) afforded a crude residue which was directly crystallized from 95% ethanol to give pure 1α-hydroxycholesta-5,7-diene acetate (51 mg, 50%)

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