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Updated: May 20, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Asymmetric synthesis of (+)-vertine and (+)-lythrine
Laëtitia Chausset-Boissarie1, Roman Àrvai, Graham R Cumming
1Department of Organic Chemistry, University of Geneva, 30, quai Ernest Ansermet, CH-1211 Geneva, Switzerland.
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.
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