Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (S)-glycidyl tosylate. Synthesis of the orally active HIV-1 protease inhibitor L-735,524

David Askin, Kan K. Eng, Kai Rossen, Robert M. Purick, Kenneth M. Wells, R. P. Volante, Paul J. Reider

Research output: Contribution to journalArticle

145 Scopus citations

Abstract

Reaction of chiral amide enolate Li-1 with (S)-glycidyl tosylate 11 affords the epoxide 3 in 72% yield with high diastereoselectivity. Epoxide 3 is converted to the orally-active HIV-1 protease inhibitor L-735,524 in 71% isolated yield.

Original languageEnglish (US)
Pages (from-to)673-676
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number5
DOIs
StatePublished - 1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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