Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 6
17
Views
13
CrossRef citations to date
0
Altmetric
Original Articles

Reduction of the Δ13-15-Keto Grouping of Prostaglandin Intermediates

, &
Pages 451-456 | Received 18 Jul 1975, Published online: 06 Dec 2006

References

  • Alfred P. Sloan Foundation Fellow . 1972–1974 . Camille and Henry Dreyfus Teacher-Scholar, 1974–1979
  • Leovey , E. M. K. and Andersen , N. H. J. Amer. Chem. Soc. , 97 in press
  • Andersen , N. H. and Ramwell , P. W. 1974 . Arch. Intern. Med. , 133 : 30
  • The synthesis of prostaglandin analogs is supported by NICH & HD contract #N01-HD-4–2839
  • Rabinowitz , I. , Ramwell , P. and Davison , P. 1971 . Nature New Biology , 233 : 88 See also 2b
  • Corey , E. J. , Albonico , S. M. , Koelliker , U. , Schaaf , T. K. and Varma , R. K. 1971 . J. Amer. Chem. Soc. , 93 : 1491
  • Andersen , N. H. and Leovey , E. M. K. 1974 . Prostaglandins , 6 : 361 A small but significant amount of 1,4-reduction has been noted previously using Zn(BH4)
  • Hayashi , M. , Miyake , H. , Tanouchi , T. , Iguchi , S. , Iguchi , Y. and Tanouchi , F. 1973 . J. Org. Chem. , 38 : 1250
  • Magerlein , B. J. , Ducharme , D. W. , Magee , W. E. , Miller , W. L. , Robert , A. and Weeks , J. R. 1973 . Prostaglandins , 4 : 143
  • Corey , E. J. , Becker , K. B. and Varma , R. V. 1972 . J. Amer. Chem. Soc. , 94 : 8616 See also 5
  • Structures established by appropriate chemical correlations. Oxidation (H2CrO4) of III-c affords III-f. Enone IV-d on being subjected to A1(OiPr)3 affords IV-a+b and V-a+b with the latter predominating on prolonged exposure
  • Newman , M. S. 1950 . J. Amer. Chem. Soc. , 72 : 4783
  • Ganem , B. 1975 . J. Org. Chem. , 40 : 146
  • Bowler , J. , Mallion , K. B. and Raphael , R. A. 1974 . Syn. Commun. , 4 : 211 A single report of the use of A1(OiPr)3 in PG synthesis appeared during the course of this work
  • June 1975 . Ph.D. thesis June , Univ. Wash. . ORD and CD data obtained using ethanol as the solvent. The values for the 17-unsubstituted series (R = H) are taken from the, of E.M.K.L

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.