Article (Scientific journals)
Enantioselective Syntheses and Absolute Configuration of the Ladybird Defence Alkaloids (+)-Calvine and (+)-2-Epicalvine
Laurent, Pascal; Braekman, Jean-Claude; Daloze, Désiré
2000In European Journal of Organic Chemistry, 11, p. 2057-2062
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Keywords :
Alkaloids; Asymmetric Synthesis; Electrochemistry; CN(R,S) method; Piperidines; Insects
Abstract :
[en] Enantiomerically pure (+)-calvine (1a) and (+)-2-epicalvine (Ib), two piperidine alkaloids isolated from ladybird beetles of the genus Calvia (Coccinellidae), were synthesized by two different strategies starting from (-)-2,3,6,7,8,8a-hexahydro-3-phenyl-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile (2). The key steps of these syntheses are the stereocontrolled formation of an asymmetric centre a to the nitrogen atom of 2 and the subsequent introduction of the methoxycarbonylmethyl substituent at the u'-position. Comparison of the optical rotations of the synthetic benzoates (12a) and (12b) with those of the corresponding benzoates derived from the natural compounds has revealed the absolute configuration of (+)-calvine to be (2S,6S) and that of (+)-2-epicalvine to be (2R,6S).
Disciplines :
Chemistry
Author, co-author :
Laurent, Pascal ;  Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Braekman, Jean-Claude
Daloze, Désiré
Language :
English
Title :
Enantioselective Syntheses and Absolute Configuration of the Ladybird Defence Alkaloids (+)-Calvine and (+)-2-Epicalvine
Alternative titles :
[en] Enantioselective Syntheses and Absolute Configuration of the Ladybird Defence Alkaloids (+)-Calvine and (+)-2-Epicalvine
Publication date :
2000
Journal title :
European Journal of Organic Chemistry
ISSN :
1434-193X
eISSN :
1099-0690
Publisher :
Wiley, Weinheim, Germany
Volume :
11
Pages :
2057-2062
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 03 June 2010

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