Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

• Luíse Azevedo,
• Larissa Faqueti,
• Marina Kritsanida,
• Antonia Efstathiou,
• Despina Smirlis,
• Gilberto C. Franchi Jr,
• Grégory Genta-Jouve,
• Sylvie Michel,
• Louis P. Sandjo,
• Raphaël Grougnet and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68

• iridoid derivatives [31], and diterpene glycosides [32]. This technique was for the first time used with Jungia extracts. Elucidation of the compounds Compound 1 was obtained as colorless gum. The molecular formula C21H30O8 was determined from its ESI–HRMS spectrum which gave the cationic ion peak [M + H

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

• Robert Hilgraf,
• Nicole Zimmermann,
• Lutz Lehmann,
• Armin Tröger and
• Wittko Francke

Beilstein J. Org. Chem. 2012, 8, 1256–1264, doi:10.3762/bjoc.8.141

• (4S,4aR,7S,7aR)-iridomyrmecin of 95–97% ee and stereochemically pure (4S,4aS,7R,7aS)-iridomyrmecin as a minor component. Keywords: Alloxysta victrix; identification; iridoid; stereoselective synthesis; trans-fused iridomyrmecin; Introduction In the course of our studies on volatile signals of the

• chiral centers complicates a stereoselective synthesis despite the small size of the molecule. Several methods have been published for the preparation of optically active cis-fused bicyclic iridoid lactones [7][8][9][10], whereas only a few syntheses of trans-fused ring systems have been reported [11

• iridomyrmecins with corresponding data of the volatile substances Y and Z – which are present in pentane extracts of heads of Alloxysta victrix – allowed their unambiguous identification as trans-fused iridomyrmecins. Coupled GC/MS analysis using FFAP as the stationary phase revealed the natural iridoid lactones

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

• Nicole Zimmermann,
• Robert Hilgraf,
• Lutz Lehmann,
• Daniel Ibarra and
• Wittko Francke

Beilstein J. Org. Chem. 2012, 8, 1246–1255, doi:10.3762/bjoc.8.140

• 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

• few approaches specifically aiming at the synthesis of trans-fused iridoid lactones have been published. Starting from (S)-pulegone (9) or its enantiomer, Wolinsky [20][21] described a route to this group of iridoids that can be applied to synthesize pure stereoisomers of dihydronepetalactones as well

• dihydronepetalactones, starting from pure enantiomers of limonene. Our approach is also superior to that starting from optically active carvone that yields the starting material for the synthesis of trans-fused iridoid lactones only as a byproduct [15]. Identification of a trans-fused dihydronepetalactone in the