title: Synthesis of crinane utilizing an allylic sulfoxide for the construction of a hydroindole ring via vinylogous C-N bond formation.
abstract: The synthesis of crinane is disclosed via intramolecular C-N bond formation by the displacement of an allylic sulfoxonium salt. The allylic sulfide precursor was synthesized by a ring-closing metathesis reaction. The quaternary carbon stereocenter was created by alkylation of a benzylic cyanide. The allyl sulfide 14 was prepared by adding vinylmagnesium bromide to an α-chlorosulfide.
authors.affiliation: Natural Products Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500007, India. sraghavan@iict.res.in.
authors.forename: Sadagopan
authors.initials: S
authors.lastname: Raghavan
authors.affiliation: Natural Products Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500007, India. sraghavan@iict.res.in.
authors.forename: Anil
authors.initials: A
authors.lastname: Ravi
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D007211:Indoles / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D012451:Safrole / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000475:Alkenes; D047151:Amaryllidaceae Alkaloids; D007211:Indoles; C504763:crinane; D002244:Carbon; D009584:Nitrogen; D012451:Safrole; C005746:sulfoxide