(2S,5S)-2,5-dibenzyl-1,4-dimethylpiperazine, a novel alkaloid from zanthoxylum arborescens
β Scribed by Jonas A. Grina; Frank R. Stermitz
- Book ID
- 104243591
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 133 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The isolation and structure determination of (2S,5S)-2,5-dibenzyl-1,4-dimethylpiperam, a new alkaloid biogenetically related to L-phenylalanine diketopiperazine, is described Dreyer investigated1 the alkaloid content of seed husks from Zanthoxylum arborescens Rose, a Mexican member of the citrus family (Rutaceae), and found two new quinazolones. We have been investigating the leaves, bark, and wood of this species and have found a number of alkaloids. The structure of one of these is described here. Dried, ground leaves were extracted with hexane and then with MeOH. The residue from the MeOH extraction was dissolved in dil. aq. H2S04. This solution was extracted with CHCl,, made
π SIMILAR VOLUMES
In the chiral title compound, C 33 H 42 N 4 O 2 S 2 , the dihedral angle between the imidazole ring planes is 79.47 (17) . The packing is consolidated by van der Waals forces and weak C-HΓ Γ ΓS interactions.
A new and concise synthesis of the useful synthetic intermediate 1 is described which also allows access to a novel C2-symmetric ketone 2. The route relies on the Sharpless asymmetric dihydroxylation of fulvenes.