A synthesis of the HIV-protease inhibitor nelfinavir from d-tartaric acid
โ Scribed by Kim F Albizati; Srinivasan Babu; Angela Birchler; Juliette K Busse; Michelle Fugett; Alan Grubbs; Aubrey Haddach; Miguel Pagan; Barbara Potts; Travis Remarchuk; Dale Rieger; Rick Rodriguez; Jim Shanley; Robert Szendroi; Tony Tibbetts; Kathleen Whitten; Bennett C Borer
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 80 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
This letter describes a new synthesis of the HIV-protease inhibitor nelfinavir. The synthesis features a selective opening of a D-tartaric acid-derived cyclic sulfate with nitrogen nucleophiles.
๐ SIMILAR VOLUMES
An ecient synthesis of nelยฎnavir 1 was developed. The synthesis features an unusual rearrangement of a 3-amidotetrahydrofuran into a functionalized oxazoline.
Diastereoselective Michael addition of ammonia to sulfoxide 3a derived from (R)-glyceraldehyde acetonide provides amine 4a, which is converted into Nelfinavir using BF 3 โขEt 2 O/NaI reduction and subsequent coupling reactions as key steps.