Jump to main content
Jump to site search

Issue 32, 2012
Previous Article Next Article

Asymmetric synthesis of (+)-vertine and (+)-lythrine

Author affiliations


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 arylaryl 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 arylaryl coupling failed.

Graphical abstract: Asymmetric synthesis of (+)-vertine and (+)-lythrine

Back to tab navigation

Supplementary files

Publication details

The article was received on 08 May 2012, accepted on 19 Jun 2012 and first published on 19 Jun 2012

Article type: Paper
DOI: 10.1039/C2OB25880C
Org. Biomol. Chem., 2012,10, 6473-6479

  •   Request permissions

    Asymmetric synthesis of (+)-vertine and (+)-lythrine

    L. Chausset-Boissarie, R. Àrvai, G. R. Cumming, L. Guénée and E. P. Kündig, Org. Biomol. Chem., 2012, 10, 6473
    DOI: 10.1039/C2OB25880C

Search articles by author