Asymmetric synthesis of the potent HIV-protease inhibitor, nelfinavir.
An asymmetric synthesis of nelfinavir is described starting from acrolein and (S)-methyl phenyl sulfoxide. The key features include (a) stereoselective preparation of a beta-protected amino-gamma,delta-unsaturated sulfoxide by the reaction of an alpha-sulfinyl carbanion with an unsaturated t-butyl sulfinylimine, (b) stereoselective bromohydrin formation using the pendant sulfoxide group as an intramolecular nucleophile, and (c) use of commercially or readily prepared inexpensive starting materials.
Raghavan
Sadagopan
S
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India. sraghavan@iict.res.in
Krishnaiah
V
V
Sridhar
B
B
D002384:Catalysis; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019888:Nelfinavir / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D017320:HIV Protease Inhibitors; D019888:Nelfinavir