• Eric William Horton
Part of the Monographs on Endocrinology book series (ENDOCRINOLOGY, volume 7)


Total chemical synthesis of all the major natural prostaglandins is now possible as a result of the elegant methods devised by E. J. Corey. The synthesis illustrated in Fig. 1 gives high yields of the prostaglandins in their natural stereochemical configuration and may prove commercially feasible for large scale production.


Total Synthesis Eicosatrienoic Acid Boron Tribromide Total Chemical Synthesis Chloromethyl Methyl 
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  1. Bagli, J. F., Bogri, T.: Prostaglandins II — An improved synthesis and structural proof of (±)-11-deoxyprostaglandin F1β. Tetrahedron Lett. No. 1, 5–10 (1967).Google Scholar
  2. Bagli, J. F., Bogri, T.: Prostaglandins III (±)-11-deoxy-13,14-dihydroprostaglandin F and F1β, a novel synthesis of prostanoic acids. Tetrahedron Lett. No. 21, 1639–1646 (1969).Google Scholar
  3. Bagli, J. F., Bogri, T., Deghenghi, R., Wiesner, K.: Prostaglandins I — Total synthesis of 9β, 15-dihydroxyprost-13-enoic acid. Tetrahedron Lett. No. 5, 465–470 (1966).Google Scholar
  4. Beal, P. F., Babcock, J. C., Lincoln, F. H.: Synthetic approaches in the prostanoic acid series. Nobel Symposium 2, Prostaglandins. Eds.: S. Bergström and B. Samuelsson. Stockholm: Almqvist and Wiksell 1967, pp. 219–230.Google Scholar
  5. Bundy, G., Lincoln, F., Nelson, N., Pike, T., Schneider, W.: Novel prostaglandin syntheses. Ann. N. Y. Acad. Sci. 180, 76–90 (1971).PubMedCrossRefGoogle Scholar
  6. Collins, P., Jung, C. J., Pappo, R.: Prostaglandin studies. The total synthesis of dl-prostaglandin B1. Israel J. Chem. 6, 839–841 (1968).Google Scholar
  7. Corey, E. J.: Total syntheses of prostaglandins. In: Proceedings of the Robert A. Welch Foundation Conferences on Chemical Research. XII. Organic Synthesis. Ed.: W. O. Milligan. Houston, Texas, 1969, pp. 51–79.Google Scholar
  8. Corey, E. J., Andersen, N. H., Carlson, R. M., Paust, J., Vedejs, E., Vlattas, I., Winter, R. E. K.: Total synthesis of prostaglandins. Synthesis of the pure dl-E1, -F1α, -F1β, -A1, and -B1 hormones. J. Amer. chem. Soc. 90, 3245–3247 (1968).CrossRefGoogle Scholar
  9. Corey, E. J., Arnold, Z., Hutton, J.: Total synthesis of prostaglandins E2 and F (dl) via a tricarbocyclic intermediate. Tetrahedron Lett. No. 4, 307–310 (1970).Google Scholar
  10. Corey, E. J., Noyori, R.: A total synthesis of prostaglandin F2a (dl) from 2-oxabi-cyclo (3.3.0) oct-6-en-3-one. Tetrahedron Lett. No. 4, 311–313 (1970).Google Scholar
  11. Corey, E. J., Noyori, R.: Schaaf, T. K.: Total synthesis of prostaglandins F1α, E1, F2α and E2 (natural forms) from a common synthetic intermediate. J. Am. chem. Soc. 92, 2586–2587 (1970).PubMedCrossRefGoogle Scholar
  12. Corey, E. J., Vlattas, I., Andersen, N. H., Harding, K.: A new total synthesis of prostaglandins of the E1 and F1 series including 11-epiprostaglandins. J. Am. chem. Soc. 90, 3247–3248 (1968) (see erratum 90, 5947 [1968]).PubMedCrossRefGoogle Scholar
  13. Corey, E. J., Vlattas, I., Harding, K.: Total synthesis of natural (levo) and enantiomeric (dextro) forms of prostaglandin E1. J. Am. chem. Soc. 91, 535–536 (1969).PubMedCrossRefGoogle Scholar
  14. Corey, E. J., Schaaf, T. K., Huber, W., Koelliker, U., Weinshenker, N. M.: Total synthesis of prostaglandins F2α and E2 as the naturally occurring forms. J. Am. chem. Soc. 92, 397–398 (1970).PubMedCrossRefGoogle Scholar
  15. Corey, E. J., Weinshenker, N. M., Schaaf, T. K., Huber, W.: Stereo-controlled synthesis of prostaglandins F2α and E2 (dl). J. Am. chem. Soc. 91, 5675–5677 (1969).PubMedCrossRefGoogle Scholar
  16. Fried, J., Heim, S., Sunder-Plassman, P., Etheredge, S. J., Santhana- krishnan, T. S., HiMizu, J.: Synthesis af 15-desoxy-7-oxa-prostaglandin F and related substances. Prostaglandin Symposium of the Worcester Foundation for Exp. Biol. Eds.: P. W. Ramwell and J. E. Shaw. New York: Interscience 1968, pp. 351–363.Google Scholar
  17. Fried, J., Santhanakrishnan, T. S., Himizu, J., Lin, C. H., Ford, S. H., Rubin, B., Grigas, E. O.: Prostaglandin antagonists: synthesis and smooth muscle activity. Nature. 223, 208–210 (1969).PubMedCrossRefGoogle Scholar
  18. Hardegger, E., Schenk, H. P., Broger, E.: Synthese der DL-Form eines natürlichen Prostaglandins. Helv. chim. Acta 50, 2501–2504 (1967).PubMedCrossRefGoogle Scholar
  19. Holden, K. G., Hwang, B., Williams, K. R., Weinstock, J., Harman, M., Weisbach, J. A.: Synthetic studies on prostaglandins. Tetrahedron Lett. No. 13, 1569–1574 (1968).Google Scholar
  20. Just, G., Simonovitch, C.: A prostaglandin synthesis. Tetrahedron Lett. No. 22, 2093–2097 (1967).Google Scholar
  21. Just, G., Simonovitch, C., Lincoln, F. H., Schneider, W. P., Axen, U., Spero, G. B., Pike, J. E.: A synthesis of prostaglandin F1α and related substances. J. Am. chem. Soc. 91, 5364–5371 (1969).PubMedCrossRefGoogle Scholar
  22. Klok, R., Pabon, H. J. J., van Dorp, D. A.: Synthesis of DL-prostaglandin B1 and its reduction product DL-prostaglandin E1–237. Recl. Trav. chim. Pays-Bas Belg. 87, 813–823 (1968).Google Scholar
  23. Nugteren, D. H., Vonkeman, H., van Dorp, D. A.: Non-enzymic conversion of all-cis-8,11,14-eicosatrienoic acid into prostaglandin E1. Recl. Trav. chim. Pays-Bas Belg. 86, 1237–1245 (1967).Google Scholar
  24. Pappo, R., Collins, P. W., Jung, C. J.: New synthetic approach in the prostaglandin field. Ann. N. Y. Acad. Sci. 180, 64–75 (1971).PubMedCrossRefGoogle Scholar
  25. Schneider, W. P., Axen, U., Lincoln, F. H., Pike, J. E., Thompson, J. L.: The total synthesis of prostaglandins. J. Am. chem. Soc. 90, 5895 – 5896 (see erratum 91, 1043) (1968).PubMedCrossRefGoogle Scholar
  26. Schneider, W. P., Axen, U., Lincoln, F. H., Pike, J. E., Thompson, J. L.: The synthesis of prostaglandin E1 and related substances. J. Am. chem. Soc. 91, 5372–5378 (1969).PubMedCrossRefGoogle Scholar
  27. Strike, D. P., Smith, H.: A novel total synthesis of ±-13,14-dihydro prostaglandin. Ann. N. Y. Acad. Sci. 180, 91–100 (1971).PubMedCrossRefGoogle Scholar
  28. Weinheimer, A. J., Spraggins, R. L.: The occurrence of two new prostaglandin derivatives (15-epi-PGA2 and its acetate, methyl ester) in the gorgonian Plexaura homomalla. Tetrahedron Lett. No. 59, 5185–5188 (1969).Google Scholar

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© Springer-Verlag Berlin · Heidelberg 1972

Authors and Affiliations

  • Eric William Horton
    • 1
  1. 1.Department of PharmacologyUniversity of EdinburghEdinburghGreat Britain

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