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Structure of Alkaloid 275A, a Novel 1-Azabicyclo[5.3.0]decane from a Dendrobatid Frog, Dendrobates lehmanni: Synthesis of the Tetrahydrodiastereomers
- Source :
- Journal of Natural Products. 64:421-427
- Publication Year :
- 2001
- Publisher :
- American Chemical Society (ACS), 2001.
-
Abstract
- The principal alkaloid 275A in skins of the Colombian poison frog Dendrobates lehmanni has been identified as the pyrrolo[1,2-a]azepane (1), the first occurrence in nature of this "izidine" system. Tetrahydro-1 proved identical to one of the four synthetic diastereomers, 2a--2d, thereby establishing that 1 has the 5Z,10E relative stereochemistry. Alkaloid 1 is often accompanied by other congeners, in particular a 5Z,10Z diastereomer 15, a dihydro analogue 16, and a ketone 17. Such izidines in frogs may arise from dietary ants, as do other classes of izidines.
- Subjects :
- Chromatography, Gas
Ketone
Stereochemistry
Pharmaceutical Science
Stereoisomerism
Chemical synthesis
Analytical Chemistry
Bridged Bicyclo Compounds
chemistry.chemical_compound
Alkaloids
Azepane
Salientia
Drug Discovery
Animals
Pharmacology
chemistry.chemical_classification
Aza Compounds
Molecular Structure
biology
Bicyclic molecule
Spectrum Analysis
Alkaloid
Organic Chemistry
Diastereomer
biology.organism_classification
Complementary and alternative medicine
chemistry
Molecular Medicine
Anura
Subjects
Details
- ISSN :
- 15206025 and 01633864
- Volume :
- 64
- Database :
- OpenAIRE
- Journal :
- Journal of Natural Products
- Accession number :
- edsair.doi.dedup.....97a8ccbb8e55c3351fe138df420f8055