title: Efficient entry into 2-substituted tetrahydroquinoline systems through alkylative ring expansion: stereoselective formal synthesis of (+/-)-martinellic acid.
abstract: A new efficient synthesis of 2-substituted tetrahydroquinolines has been achieved by the domino reaction of N-indanyl(methoxy)amines, which consists of three types of reactions: elimination of an alcohol, the rearrangement of an aryl group, and the addition of an organolithium or magnesium reagent. The synthetic utility of this approach is demonstrated by the stereoselective formal synthesis of (+/-)- martinellic acid.
authors.affiliation: Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
authors.forename: Masafumi
authors.initials: M
authors.lastname: Ueda
authors.forename: Sayuri
authors.initials: S
authors.lastname: Kawai
authors.forename: Masataka
authors.initials: M
authors.lastname: Hayashi
authors.forename: Takeaki
authors.initials: T
authors.lastname: Naito
authors.forename: Okiko
authors.initials: O
authors.lastname: Miyata
mesh_terms: D000478:Alkylation; D002384:Catalysis; D008094:Lithium / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009942:Organometallic Compounds; D011758:Pyrroles; D011804:Quinolines; C432345:martinellic acid; D008094:Lithium; C542964:1,2,3,4-tetrahydroquinoline; D008274:Magnesium