Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides: Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate

P. E. Maligres, V. Upadhyay, K. Rossen, S. J. Cianciosi, R. M. Purick, K. K. Eng, R. A. Reamer, D. Askin, R. P. Volante, P. J. Reider

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Abstract

Reaction of 2-alkyl-4-enamides 2, 9-15 with NIS and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins 3, 16-22 with essentially no iodolactone by-product. This methodology has been successfully employed for the synthesis of the epoxide intermediate 4 of the orally active Merck HIV-1 protease inhibitor L-735,524.

Original languageEnglish (US)
Pages (from-to)2195-2198
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number13
DOIs
StatePublished - Mar 27 1995
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Maligres, P. E., Upadhyay, V., Rossen, K., Cianciosi, S. J., Purick, R. M., Eng, K. K., Reamer, R. A., Askin, D., Volante, R. P., & Reider, P. J. (1995). Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides: Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate. Tetrahedron Letters, 36(13), 2195-2198. https://doi.org/10.1016/0040-4039(95)00273-F