title: Asymmetric synthesis of the potent HIV-protease inhibitor, nelfinavir.
abstract: 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.
authors.affiliation: Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India. sraghavan@iict.res.in
authors.forename: Sadagopan
authors.initials: S
authors.lastname: Raghavan
authors.forename: V
authors.initials: V
authors.lastname: Krishnaiah
authors.forename: B
authors.initials: B
authors.lastname: Sridhar
mesh_terms: D002384:Catalysis; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019888:Nelfinavir / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D017320:HIV Protease Inhibitors; D019888:Nelfinavir