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1 article(s) from Ibarra, Daniel

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

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Figure 1: Terpenoids 1–5 present in Alloxysta victrix and cis-fused bicyclic iridoids known from other insect...

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Figure 2: 70 eV EI-mass spectrum of the iridoid X, a component of the volatile secretions of the parasitoid w...

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Figure 3: Structures and gas chromatographic retention times of trans-fused dihydronepetalactones on a conven...

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Scheme 1: Route from (S)-pulegone to the mixture of dihydronepetalactones a and b, consequently following Wol...

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Figure 4: Configuration of the dihydronepetalactone a.

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Figure 5: Route to stereochemically pure trans-fused dihydronepetalactones a–d from (R)-limonene.

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Scheme 2: Synthesis of the key compound 16. Reaction conditions: a) O₃, MeOH, −50 °C (86%); b) AcOH, piperidi...

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Scheme 3: Synthesis of trans,trans-substituted dihydronepetalactone b. Reaction conditions: a) TBDMSCl, imida...

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Figure 6: Configurations of compound 24 and the dihydronepetalactone b.

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Scheme 4: Synthesis of cis,trans-substituted dihydronepetalactone c. Reaction conditions: a) Crabtree's catal...

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Figure 7: Configurations of compound 26 and the dihydronepetalactone c.

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Scheme 5: Synthesis of a 2:3 mixture of dihydronepetalactones c and d. Reaction conditions: a) (COCl)₂, DMSO,...

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Scheme 6: Formal synthesis of a mixture of dihydronepetalactones a and b from (R)-limonene.

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Published 07 Aug 2012

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