title: Catalytic Dearomatization Approach to Quinolizidine Alkaloids: Five Step Total Synthesis of (±)-Lasubine II.
abstract: A series of high-yielding silver(I)-catalyzed cyclization reactions of pyridine-, isoquinoline-, and pyrazine-ynones are described. The operationally simple and mild reaction conditions are a significant improvement over previously reported thermal cyclizations. The quinolizinone products were also used in a novel dearomatization strategy to prepare 0.53 g of the alkaloid lasubine II in five steps and 36% overall yield.
authors.affiliation: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: James
authors.affiliation: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors.forename: Niall D
authors.initials: ND
authors.lastname: Grant
authors.affiliation: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors.forename: Peter
authors.initials: P
authors.lastname: O'Brien
authors.affiliation: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors.forename: Richard J K
authors.initials: RJ
authors.lastname: Taylor
authors.affiliation: Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.
authors.forename: William P
authors.identifier: 0000-0002-9169-5156
authors.initials: WP
authors.lastname: Unsworth