| Title: | "Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones" |
| Author(s): | Zimmermann N; Hilgraf R; Lehmann L; Ibarra D; Francke W; |
| Address: | "Department of Chemistry - Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany" |
| ISSN/ISBN: | 1860-5397 (Electronic) 1860-5397 (Linking) |
| Abstract: | "Starting from the enantiomers of limonene, all eight stereoisomers of trans-fused dihydronepetalactones were synthesized. Key compounds were pure stereoisomers of 1-acetoxymethyl-2-methyl-5-(2-hydroxy-1-methylethyl)-1-cyclopentene. The stereogenic center of limonene was retained at position 4a of the target compounds and used to stereoselectively control the introduction of the other chiral centers during the synthesis. Basically, this approach could also be used for the synthesis of enantiomerically pure trans-fused iridomyrmecins. Using synthetic reference samples, the combination of enantioselective gas chromatography and mass spectrometry revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain the enantiomerically pure trans-fused (4R,4aR,7R,7aS)-dihydronepetalactone as a minor component, showing an unusual (R)-configured stereogenic center at position 7" |
| Keywords: | Alloxysta victrix identification iridoid stereoselective synthesis trans-fused dihydronepetalactone; |
| Notes: | "PubMed-not-MEDLINEZimmermann, Nicole Hilgraf, Robert Lehmann, Lutz Ibarra, Daniel Francke, Wittko eng Germany 2012/09/29 Beilstein J Org Chem. 2012; 8:1246-55. doi: 10.3762/bjoc.8.140. Epub 2012 Aug 7" |
