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

Published in Organic and Biomolecular Chemistry. 2012, vol. 10, no. 32, p. 6473-6479
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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CHAUSSET BOISSARIE, Laetitia Laure et al. Asymmetric synthesis of (+)-vertine and (+)-lythrine. In: Organic and Biomolecular Chemistry, 2012, vol. 10, n° 32, p. 6473-6479. doi: 10.1039/c2ob25880c https://archive-ouverte.unige.ch/unige:21968

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Deposited on : 2012-08-08

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