✦ LIBER ✦
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
✍ Scribed by David Askin; Kan K Eng; Kai Rossen; Robert M Purick; Kenneth M Wells; R.P Volante; Paul J Reider
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 305 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Reaction of chiral amide e&ate L&I with (S)-iyci&l tosylate I1 qj?ordt the epoxide 3 in 72% yield with high diastereoselectivity. Epoxide 3 is converte % to the orally-active WV-I protease inhibitor L-735,524 in 71% isolated yield.
Hydroxyetbylene dipeptide isosteres which contain the 1S,2R-1-amino-2-hydroxy-indanamide (AHI) moiety can be potent inhibitors of HIV-1 protease. * A highly diastereoselective route to the 2(R)-aryl-4(S)-hydroxy AH1
isosteres was recently developed via alkylation of (N-Boc)-a-amino-epoxides with the n-BuLi generated enolate
Li-1 (Scheme I>.2