title: A Conia-Ene-Type Cyclization under Basic Conditions Enables an Efficient Synthesis of (-)-Lycoposerramine R.
abstract: An enantioselective total synthesis of the Lycopodium alkaloid lycoposerramine R is presented. It relies on a base-mediated cyclization that resembles the Conia-ene reaction of ynones and gold-catalyzed variants thereof. Thus, hydrindanones and other functionalized ring systems bearing an exocyclic alkene can be rapidly accessed at room temperature without noble metal catalysis or substrate preactivation.
authors.affiliation: Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377, München, Germany.
authors.forename: Felix W W
authors.initials: FW
authors.lastname: Hartrampf
authors.affiliation: Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377, München, Germany.|Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Furukawa
authors.affiliation: Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377, München, Germany.
authors.forename: Dirk
authors.identifier: 0000-0002-6782-6056
authors.initials: D
authors.lastname: Trauner
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D032502:Lycopodium / Q000737:chemistry*; D008968:Molecular Conformation; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D011728:Pyridones; C551369:lycoposerramine R
keywords: Conia-ene reaction; alkynes; hydrindanes; lycopodium alkaloids; total synthesis