Journal article
Asymmetric synthesis of (+)-vertine and (+)-lythrine.
- Chausset-Boissarie L Department of Organic Chemistry, University of Geneva, 30, quai Ernest Ansermet, CH-1211 Geneva, Switzerland.
- Àrvai R
- Cumming GR
- Guénée L
- Kündig EP
- 2012-07-06
Published in:
- Organic & biomolecular chemistry. - 2012
English
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.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1039/c2ob25880c
- PMID 22763639
- Persistent URL
- https://folia.unifr.ch/global/documents/240430
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