title: Asymmetric Synthesis of a Potent HIV-1 Integrase Inhibitor.
abstract: The development of a practical asymmetric total synthesis of the potent HIV-1 integrase inhibitor 5 is described. Key transformations include construction of the naphthridine core in a highly efficient manner followed by cyclization of the 8-membered ring. Control of the atropisomers of intermediates and final compound 5 is also described.
authors.affiliation: Department of Process Chemistry, Merck & Co., Inc. P.O. Box 2000, Rahway, New Jersey 07065, United States.
authors.forename: Jeffrey T
authors.initials: JT
authors.lastname: Kuethe
authors.affiliation: Department of Process Chemistry, Merck & Co., Inc. P.O. Box 2000, Rahway, New Jersey 07065, United States.
authors.forename: Guy R
authors.initials: GR
authors.lastname: Humphrey
authors.affiliation: Department of Process Chemistry, Merck & Co., Inc. P.O. Box 2000, Rahway, New Jersey 07065, United States.
authors.forename: Michel
authors.initials: M
authors.lastname: Journet
authors.affiliation: Department of Process Chemistry, Merck & Co., Inc. P.O. Box 2000, Rahway, New Jersey 07065, United States.
authors.forename: Zhihui
authors.initials: Z
authors.lastname: Peng
authors.affiliation: Department of Process Chemistry, Merck & Co., Inc. P.O. Box 2000, Rahway, New Jersey 07065, United States.
authors.forename: Karla G
authors.initials: KG
authors.lastname: Childers
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D003500:Cyclization; D019427:HIV Integrase / Q000187:drug effects*; D019428:HIV Integrase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009287:Naphthyridines / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy
chemical_list: D019428:HIV Integrase Inhibitors; D009287:Naphthyridines; D019427:HIV Integrase; C514801:p31 integrase protein, Human immunodeficiency virus 1