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Issue 32, 2012
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Asymmetric synthesis of (+)-vertine and (+)-lythrine

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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 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

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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
Citation: Org. Biomol. Chem., 2012,10, 6473-6479
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    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

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