title: Asymmetric synthesis of (+)-vertine and (+)-lythrine.
abstract: The total syntheses of the Lythracea alkaloids (+)-vertine and (+)-lythrine are described. Enantioenriched pelletierine is used as a chiral building block and engaged into a two step pelletierine condensation leading to two quinolizidin-2-one diastereomers in a 8 : 1 ratio. The major product is used in the synthesis of (+)-vertine via aryl-aryl coupling and ring closing metathesis to provide a Z-alkene α to the lactone carbonyl function. The same procedure was used for (+)-lythrine after base induced epimerization of the main quinolizidin-2-one diastereomer. Alternative classical ring closure strategies like macrolactonisation or aryl-aryl coupling failed.
authors: Department of Organic Chemistry, University of Geneva, 30, quai Ernest Ansermet, CH-1211 Geneva, Switzerland.
authors: Laëtitia
authors: L
authors: Chausset-Boissarie
authors: Roman
authors: R
authors: Àrvai
authors: Graham R
authors: GR
authors: Cumming
authors: Laure
authors: L
authors: Guénée
authors: E Peter
authors: EP
authors: Kündig
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D029561:Lythraceae / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000470:Alkaloids; D010880:Piperidines; C008195:isopelletierine; C000519:cryogenine; C576487:lythrine