title: Natural products as templates for bioactive compound libraries: part 2. Novel modifications of vasicine (peganine) core via efficient and regioselective generation of 3-lithiodeoxyvasicine and its stereoselective addition to aliphatic ketones section sign.
abstract: A general procedure for direct lithiation of deoxyvasicine was developed. 3-Lithiodeoxyvasicine intermediate was found to react with various aliphatic ketones providing derivatives of 3-(hydroxyalkyl)deoxyvasicine in good yields. Similar reaction with 4-alkylcyclohexanones yielded respective trans-adducts exclusively. This novel protocol was successfully scaled-up to result in multigram quantities of vasicine-containing core building blocks suitable for production of compound libraries. The described synthetic methodology offers access to a wide range of compounds with potentially beneficial biological profiles.
authors.affiliation: Chemical Diversity Research Institute, Khimki, Moscow Reg., 114401 Russia.
authors.forename: Sergey V
authors.initials: SV
authors.lastname: Shevyakov
authors.forename: Olga I
authors.initials: OI
authors.lastname: Davydova
authors.forename: Alex S
authors.initials: AS
authors.lastname: Kiselyov
authors.forename: Dmitry V
authors.initials: DV
authors.lastname: Kravchenko
authors.forename: Alexandre V
authors.initials: AV
authors.lastname: Ivachtchenko
authors.forename: Mikhail
authors.initials: M
authors.lastname: Krasavin
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D007659:Ketones / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011799:Quinazolines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D007659:Ketones; D011799:Quinazolines; C019592:vasicine; D008094:Lithium