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Beilstein J. Org. Chem. 2012, 8, 1256–1264, doi:10.3762/bjoc.8.141
Graphical Abstract
Figure 1: Structures of cis- and trans-fused iridoid lactones.
Figure 2: 70 eV EI-mass spectrum of compounds Y and Z of Alloxysta victrix.
Figure 3: Chemical structures of all eight stereoisomers of trans-fused iridomyrmecins and their gas chromato...
Figure 4: Strategy for the stereoselective synthesis of trans-fused iridomyrmecins A–D from (R)-limonene.
Scheme 1: Synthesis of the trans-fused iridomyrmecins A and B. Reaction conditions and yields: a) ammonium fo...
Figure 5: Configurations of the trans-fused iridomyrmecins A and B’.
Scheme 2: Synthesis of the trans-fused iridomyrmecins C and D. Reaction conditions and yields: a) Crabtree's ...
Figure 6: Configurations of the trans-fused iridomyrmecins C and D’.
Figure 7: Volatile terpenoids in the cephalic secretion of Alloxysta victrix. For the identification of compo...
Figure 8: Structures of iridoids from insects and plants. Absolute configurations of 19 and 20 are "educated ...
Figure 9: Biosynthetic ways to iridoids from geraniol.
Beilstein J. Org. Chem. 2012, 8, 1246–1255, doi:10.3762/bjoc.8.140
Figure 1: Terpenoids 1–5 present in Alloxysta victrix and cis-fused bicyclic iridoids known from other insect...
Figure 2: 70 eV EI-mass spectrum of the iridoid X, a component of the volatile secretions of the parasitoid w...
Figure 3: Structures and gas chromatographic retention times of trans-fused dihydronepetalactones on a conven...
Scheme 1: Route from (S)-pulegone to the mixture of dihydronepetalactones a and b, consequently following Wol...
Figure 4: Configuration of the dihydronepetalactone a.
Figure 5: Route to stereochemically pure trans-fused dihydronepetalactones a–d from (R)-limonene.
Scheme 2: Synthesis of the key compound 16. Reaction conditions: a) O3, MeOH, −50 °C (86%); b) AcOH, piperidi...
Scheme 3: Synthesis of trans,trans-substituted dihydronepetalactone b. Reaction conditions: a) TBDMSCl, imida...
Figure 6: Configurations of compound 24 and the dihydronepetalactone b.
Scheme 4: Synthesis of cis,trans-substituted dihydronepetalactone c. Reaction conditions: a) Crabtree's catal...
Figure 7: Configurations of compound 26 and the dihydronepetalactone c.
Scheme 5: Synthesis of a 2:3 mixture of dihydronepetalactones c and d. Reaction conditions: a) (COCl)2, DMSO,...
Scheme 6: Formal synthesis of a mixture of dihydronepetalactones a and b from (R)-limonene.