1393603-33-2Relevant academic research and scientific papers
Asymmetric synthesis of (+)-vertine and (+)-lythrine
Chausset-Boissarie, La?titia,àrvai, Roman,Cumming, Graham R.,Guénée, Laure,Kündig, E. Peter
, p. 6473 - 6479 (2012/09/08)
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.
