title: Short Total Synthesis of (±)-γ-Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction.
abstract: An intramolecular acylal cyclisation (IAC) approach to the synthesis of a range of bicyclic heterocycles is reported. As an example of the utility of the IAC reaction, the methodology was applied in a protecting-group-free five-step total synthesis of (±)-γ-lycorane, incorporating a new intramolecular Heck addition reaction to generate the pentacyclic core structure of the natural product in good yield.
authors.affiliation: UCL School of Pharmacy, University College London, 29-39 Brunswick Square, London, WC1N 1AX, UK.
authors.forename: Alessandra
authors.initials: A
authors.lastname: Monaco
authors.affiliation: UCL School of Pharmacy, University College London, 29-39 Brunswick Square, London, WC1N 1AX, UK.
authors.forename: Blanka R
authors.initials: BR
authors.lastname: Szulc
authors.affiliation: UCL School of Pharmacy, University College London, 29-39 Brunswick Square, London, WC1N 1AX, UK.
authors.forename: Zenobia X
authors.initials: ZX
authors.lastname: Rao
authors.affiliation: Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia, Institute of Biomedicine (IBUB), Universitat de Barcelona, Av. Joan XXIII, s/n, 08028, Barcelona, Spain.
authors.forename: Marta
authors.initials: M
authors.lastname: Barniol-Xicota
authors.affiliation: UCL School of Pharmacy, University College London, 29-39 Brunswick Square, London, WC1N 1AX, UK.
authors.forename: Moussa
authors.initials: M
authors.lastname: Sehailia
authors.affiliation: UCL School of Pharmacy, University College London, 29-39 Brunswick Square, London, WC1N 1AX, UK.
authors.forename: Bruno M A
authors.initials: BM
authors.lastname: Borges
authors.affiliation: UCL School of Pharmacy, University College London, 29-39 Brunswick Square, London, WC1N 1AX, UK.
authors.forename: Stephen T
authors.identifier: http://orcid.org/0000-0001-8782-4499
authors.initials: ST
authors.lastname: Hilton
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D003500:Cyclization; D058116:Lewis Acids / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D047151:Amaryllidaceae Alkaloids; D056831:Coordination Complexes; D058116:Lewis Acids; C412290:lycorane; D010165:Palladium
keywords: Heck reaction; Lewis acids; erythrina; lycoranes; tandem cyclisation