title: Stereoselective hydroazidation of amino enones: synthesis of the ritonavir/lopinavir core.
abstract: [reaction: see text] The base-catalyzed hydroazidation of alpha'-amino alpha,beta-unsaturated ketones with in situ generated hydrazoic acid was found to proceed with high stereoselectivity in favor of the syn product. The stereoselectivity is controlled by the configuration of the enone and syn/anti ratios up to 7:1 were obtained with secondary and tertiary amines at low temperature. By this route the diamino alcohol core of HIV-PR inhibitors ritonavir and lopinavir was synthesized in 37% yield from phenylalanine.
authors.affiliation: Department of Chemical Sciences, University of Trieste, Italy.
authors.forename: Ilaria
authors.initials: I
authors.lastname: Adamo
authors.forename: Fabio
authors.initials: F
authors.lastname: Benedetti
authors.forename: Federico
authors.initials: F
authors.lastname: Berti
authors.forename: Pietro
authors.initials: P
authors.lastname: Campaner
mesh_terms: D001386:Azides / Q000737:chemistry*; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D061466:Lopinavir; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D019438:Ritonavir / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001386:Azides; D017320:HIV Protease Inhibitors; D011744:Pyrimidinones; D061466:Lopinavir; D019438:Ritonavir