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

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...

Full description

Saved in:
Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 10; no. 32; pp. 6473 - 6479
Main Authors Chausset-Boissarie, Laetitia, Arvai, Roman, Cumming, Graham R., Guenee, Laure, Kuendig, E. Peter
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.08.2012
Subjects
Alkaloids - chemical synthesis
Alkaloids - chemistry
Chemistry
Chemistry, Organic
Lythraceae - chemistry
Models, Molecular
Molecular Structure
Physical Sciences
Piperidines - chemical synthesis
Piperidines - chemistry
Science & Technology
SELECTIVE DEPROTECTION
Z-UNSATURATED ESTERS
RING-CLOSING METATHESIS
DECODON-VERTICILLATUS
COUPLING REACTIONS
NATURAL-PRODUCTS
QUINOLIZIDINE-ALKALOIDS
METHOXYMETHYL MOM ETHERS
LYTHRACEAE ALKALOIDS
HEIMIA-SALICIFOLIA
Online AccessGet full text

Cover

More Information
Summary: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 alpha 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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25880c