Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins

Following our earlier approach to the synthesis of dihydronepetalactones, all eight stereoisomers of trans-fused iridomyrmecins were synthesized starting from the enantiomers of limonene. Combined gas chromatography and mass spectrometry including enantioselective gas chromatography revealed that vo...

Descripción completa

Detalles Bibliográficos
Autores principales: Hilgraf, Robert, Zimmermann, Nicole, Lehmann, Lutz, Tröger, Armin, Francke, Wittko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458746/
https://www.ncbi.nlm.nih.gov/pubmed/23019456
http://dx.doi.org/10.3762/bjoc.8.141
_version_ 1782244693409529856
author Hilgraf, Robert
Zimmermann, Nicole
Lehmann, Lutz
Tröger, Armin
Francke, Wittko
author_facet Hilgraf, Robert
Zimmermann, Nicole
Lehmann, Lutz
Tröger, Armin
Francke, Wittko
author_sort Hilgraf, Robert
collection PubMed
description Following our earlier approach to the synthesis of dihydronepetalactones, all eight stereoisomers of trans-fused iridomyrmecins were synthesized starting from the enantiomers of limonene. Combined gas chromatography and mass spectrometry including enantioselective gas chromatography revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain (4S,4aR,7S,7aR)-iridomyrmecin of 95–97% ee and stereochemically pure (4S,4aS,7R,7aS)-iridomyrmecin as a minor component.
format Online
Article
Text
id pubmed-3458746
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-34587462012-09-27 Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins Hilgraf, Robert Zimmermann, Nicole Lehmann, Lutz Tröger, Armin Francke, Wittko Beilstein J Org Chem Full Research Paper Following our earlier approach to the synthesis of dihydronepetalactones, all eight stereoisomers of trans-fused iridomyrmecins were synthesized starting from the enantiomers of limonene. Combined gas chromatography and mass spectrometry including enantioselective gas chromatography revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain (4S,4aR,7S,7aR)-iridomyrmecin of 95–97% ee and stereochemically pure (4S,4aS,7R,7aS)-iridomyrmecin as a minor component. Beilstein-Institut 2012-08-08 /pmc/articles/PMC3458746/ /pubmed/23019456 http://dx.doi.org/10.3762/bjoc.8.141 Text en Copyright © 2012, Hilgraf et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Hilgraf, Robert
Zimmermann, Nicole
Lehmann, Lutz
Tröger, Armin
Francke, Wittko
Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins
title Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins
title_full Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins
title_fullStr Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins
title_full_unstemmed Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins
title_short Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins
title_sort stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp alloxysta victrix, part ii: iridomyrmecins
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458746/
https://www.ncbi.nlm.nih.gov/pubmed/23019456
http://dx.doi.org/10.3762/bjoc.8.141
work_keys_str_mv AT hilgrafrobert stereoselectivesynthesisoftransfusediridoidlactonesandtheiridentificationintheparasitoidwaspalloxystavictrixpartiiiridomyrmecins
AT zimmermannnicole stereoselectivesynthesisoftransfusediridoidlactonesandtheiridentificationintheparasitoidwaspalloxystavictrixpartiiiridomyrmecins
AT lehmannlutz stereoselectivesynthesisoftransfusediridoidlactonesandtheiridentificationintheparasitoidwaspalloxystavictrixpartiiiridomyrmecins
AT trogerarmin stereoselectivesynthesisoftransfusediridoidlactonesandtheiridentificationintheparasitoidwaspalloxystavictrixpartiiiridomyrmecins
AT franckewittko stereoselectivesynthesisoftransfusediridoidlactonesandtheiridentificationintheparasitoidwaspalloxystavictrixpartiiiridomyrmecins

Ejemplares similares