title: An efficient chiral moderator prepared from inexpensive (+)-3-carene: synthesis of the HIV-1 non-nucleoside reverse transcriptase inhibitor DPC 963.
abstract: The beta-amino alcohol 4 beta-morpholinocaran-3 alpha-ol is prepared by addition of morpholine to alpha-3,4-epoxycarane utilizing anhydrous magnesium bromide as Lewis acid promoter. The enantiopure amino alcohol is uniquely effective as a chiral moderator for the addition of lithium cyclopropylacetylide to an unprotected N-acylketimine. This reaction provides an efficient route to the second generation NNRTI drug candidate DPC 963.
authors.affiliation: DuPont Pharmaceuticals Company, Chemical Process R&D, Chambers Works, PRF Building S1, Deepwater, New Jersey 08023, USA.
authors.forename: G S
authors.initials: GS
authors.lastname: Kauffman
authors.forename: G D
authors.initials: GD
authors.lastname: Harris
authors.forename: R L
authors.initials: RL
authors.lastname: Dorow
authors.forename: B R
authors.initials: BR
authors.lastname: Stone
authors.forename: R L
authors.initials: RL
authors.lastname: Parsons
authors.forename: J A
authors.initials: JA
authors.lastname: Pesti
authors.forename: N A
authors.initials: NA
authors.lastname: Magnus
authors.forename: J M
authors.initials: JM
authors.lastname: Fortunak
authors.forename: P N
authors.initials: PN
authors.lastname: Confalone
authors.forename: W A
authors.initials: WA
authors.lastname: Nugent
mesh_terms: D015497:HIV-1 / Q000201:enzymology*; D015363:Quinolones / Q000138:chemical synthesis*; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C415683:DPC 963; D015363:Quinolones; D018894:Reverse Transcriptase Inhibitors