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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 4, 1974 - Issue 6
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Original Articles

A Synthesis of 2-(6′-Carboxy-2′-cis-Hexenyl)-4-Hydroxycyclopent-2-EN-1-ONE, a Prostagiandin Intermediate1

Pages 317-323 | Published online: 05 Dec 2006

References

  • Prostaglandins and Congeners VI. For Paper V, See Reference 2a
  • Bernady , K. F. and Weiss , M. J. 1973 . Prostaglandins , 3 : 505 For alanate and Grignard addition reactions see, and previous papers in that series
  • Sih , C. H. , Heather , J. B. , Peruzzotti , G. P. , Price , P. , Sood , R. and Lee , L. -F. H. 1973 . J. Amer. Chem. Soc. , 95 : 1676 For cuprate addition reactions see, and previous papers in that series; also A. F. Kluge, K. G. Untch, and J. M. Fried, J. Amer. Chem. Soc., 94, 7827 (1972); A. F. Kluge, K. G. Untch, and J. M. Fried, J. Amer. Chem. Soc., 94, 9256 (1972)
  • Pappo , R. and Collins , P. W. 1972 . Tetrahedron Letters , : 2627 For addition of a vinyl copper reagent, see
  • Heslinga , L. , van Gorkom , M. and van Dorp , D. A. 1968 . Rec. Trav. Chim. , 87 : 1421 The parent hydroxyacid was first prepared by
  • Heather , J. B. , Sood , R. , Price , P. , Peruzzotti , G. P. , Lee , S. S. , Lee , L. -F.H. and Sih , C. J. 1973 . Tetrahedron letters. , : 2313 A synthesis of l-PGE2 has been reported which utilizes the methyl ester of 3:
  • Grieco , P. A. and Reap , J. J. 1973 . J. Org. Chem. , 38 : 3413 A synthesis of dl-11-Deoxyprostaglandin E2 methyl ester has been reported which utilizes intermediate 4:
  • Bentley , P. H. For a recent review, see, Chem. Soc. Reviews, 2, 29 (1973)
  • Corey , E. J. , Arnold , Z. and Hutton , J. 1970 . Tetrahedron Letters , : 307
  • Grieco , P. A. 1972 . J. Org. Chem. , 37 : 2363
  • Waukesha, Wisc. : Commercially available from Willow Brook laboratories, Inc. .
  • Corey , E. J. and Noyori , R. 1970 . Tetrahedron letters , : 311
  • Partridge , J. J. , Chadha , N. K. and Uskokovic , M. R. 1973 . J. Amer. Chem. Soc. , 95 : 7171
  • Corey , E. J. , Weinshenker , N. M. , Schaaf , T. K. and Huber , W. 1969 . J. Amer. Chem. Soc. , 91 : 5675
  • All pmr spectra were determined in CDCl3 solution. The ir and pmr spectra and analytical data were fully consistent with the assigned structures
  • Chamberlain , P. and Whitman , G. M. 1969 . J. Chem. Soc. (B) , : 1131
  • Andersen , N. H. 1969 . J. Lipid Res. , 10 : 320 PGE compounds provide a good example:
  • Monkhouse , D. C. , Van Campen , L. and Aguiar , A. J. 1973 . J. Pharm. Sci. , 62 : 576
  • Barton , D. H. R. and Houminer , K. 1972 . J. Chem. Soc., Perkin Trans. , 1 : 919
  • Crombie , L. , Hemesley , P. and Pattenden , G. 1969 . J. Chem. Soc. (C) , : 1016
  • Bïchi , G. , Minster , D. and Young , J. C. F. 1971 . J. Amer. Chem. Soc. , 93 : 4319
  • Woessner , W. D. and Ellison , R. A. 1972 . Tetrahedron letters , : 3735

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