Skip to main content
SpringerLink
Log in

Prostanoids: XC. Extension to the Synthesis of Enprostil of the o-Nitrophenylsulfonylhydrazine Method for Transformation of 2-Propynyl Alcohols into Allenes

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

A potential precursor of enprostil, (±)-9-acetoxy-11,15-di-O-(tert-butyldimethylsilyl)-2-decarboxy-6-hydroxy-16-phenoxy-2-triphenylmethyloxymethyl-4,4,5,5-tetradehydro-17,18,19,20-tetranorprostaglandin F1α, was synthesized. This compound remained unchanged under the conditions for generation of allenes from 2-propynyl alcohols by the action of the system diisopropyl azodicarboxylate-triphenylphosphine-o-nitrophenylsulfonylhydrazine.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Vostrikov, N.S., Vasikov, V.Z., and Miftakhov, M.S., Russ. J. Org. Chem., 2004, vol. 40, p. 1539.

    Article  Google Scholar 

  2. Muchowski, J.M. and Fried, J.H., US Patent no. 3 985 791, 1977; Chem. Abstr., 1977, vol. 86, no. 43 281 k.

  3. Van Horn, A.R., Garay, G., and Edwards, J.A., US Patent no. 4 178 457, 1980; Chem. Abstr., 1981, vol. 92, no. 146 339 p.

  4. Collins, P.W. and Weiter, R.M., US Patent no. 4 689 419, 1987; Chem. Abstr., 1988, vol. 108, no. 5778 t.

  5. Collins, P.W. and Djuric, S.W., Chem. Rev., 1993, vol. 93, p. 1533.

    Article  Google Scholar 

  6. Advances in Prostaglandin, Thromboxane, and Leukotriene Research, Pike, J.E. and Morton, D.R., Eds., New York: Raven, 1985, vol. 14, p. 263.

    Google Scholar 

  7. Myers, A.G. and Zheng, B., J. Am. Chem. Soc., 1996, vol. 118, p. 4492.

    Article  Google Scholar 

  8. Mitsunobu, O., Synthesis, 1981, no. 1, p. 1.

  9. Lin, C.H. and Alexander, D.L., J. Org. Chem., 1982, vol. 47, p. 615.

    Google Scholar 

  10. Luche, J.-L., J. Am. Chem. Soc., 1978, vol. 100, p. 2226.

    Article  Google Scholar 

  11. Wahlstorm, I.L. and Ronald, R.C., J. Org. Chem., 1998, vol. 63, p. 6021.

    Article  PubMed  Google Scholar 

  12. Vadav, J.S. and Subba Reddy, B.V., Carbohydr. Res., 2000, vol. 329, p. 885.

    Article  PubMed  Google Scholar 

  13. Kocienski, Ph.J., Protecting Groups, Stuttgart: Thieme, 1994, p. 54.

    Google Scholar 

  14. Carlock, J.T. and Mack, M.P., Tetrahedron Lett., 1978, vol. 52, p. 5153.

    Article  Google Scholar 

  15. Thiery, J.-Ch., Frechou, C., and Demailly, G., Tetrahedron Lett., 2000, vol. 41, p. 6337.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, Bashkortostan, 450054, Russia

    N. S. Vostrikov, V. Z. Vasikov & M. S. Miftakhov

Authors
  1. N. S. Vostrikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. Z. Vasikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. S. Miftakhov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 7, 2005, pp. 988–994.

Original Russian Text Copyright © 2005 by Vostrikov, Vasikov, Miftakhov.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vostrikov, N.S., Vasikov, V.Z. & Miftakhov, M.S. Prostanoids: XC. Extension to the Synthesis of Enprostil of the o-Nitrophenylsulfonylhydrazine Method for Transformation of 2-Propynyl Alcohols into Allenes. Russ J Org Chem 41, 967–973 (2005). https://doi.org/10.1007/s11178-005-0278-8

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11178-005-0278-8

Keywords

Search

Navigation