Erysodienone
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Comment: The synthesis of the compound is covered, but there is no indication of what makes this process special. Wikipedia is not a guide or journal. Primefac (talk) 20:17, 26 January 2015 (UTC)
Erysodienone is a key precursor in the biosynthesis of many Erythrina-produced alkaloids.[1] Early work was done by Derek Barton and co-workers to illustrate the biosynthetic pathways towards erythrina alkaloids.[2][3][4] It was demonstrated that erysodienone could be synthesized from simple starting materials by a similar approach as its biosynthetic pathway, which lead to the development of the biomimetic synthesis of erysodienone.[5]
Synthesis
The biosynthesis of erysodienone involves a key step of oxidative phenol coupling. Starting with S-norprotosinomenine precursor A, cyclization via oxidative phenol coupling forms intermediate B, which in turn can be rearranged to form intermediate C. Hydrogenation of C forms the diphenoquinone intermediate E. An intramolecular Michael addition reaction converts E to the final product, erysodienone.[6]
A biomimetic synthesis route for erysodienone was developed based on a similar oxidative phenol coupling mechanism. Barton and co-workers[7] found that treating bisphenolethylamine precursor F with oxidants such as K3Fe(CN)6 initiated oxidative phenol coupling to form the 9-membered ring structure in intermediate D that itself undergo a Michael addition to give erysodienone.[8]
References
- ^ Rahman, Mohammed Z., et al. "Phytochemical and biological investigations of Erythrina variegata." Saudi Pharmaceutical Journal 15.2 (2007): 140.
- ^ Barton, D. H. R.; Boar, R. B.; Widdowson, D. A. J. Chem. Soc. C 1970, 1213.
- ^ Barton, D. H. R.; Potter, C. J.; Widdowson, D. A. J. Chem. Soc. Perkin. Trans. 1974, 1346.
- ^ Barton, D. H. R.; James, R.; Kirby, G. W.; Turner, D. W.; Widdowson, D. A. J. Chem. Soc. C 1968, 1529.
- ^ Herbert, R. B. (1985). "The Biosynthesis of Isoquinoline Alkaloids": 213–228. doi:10.1007/978-3-642-70128-3_14. ISSN 0172-6625.
{{cite journal}}: Cite journal requires|journal=(help) - ^ Maier UH, Rödl W, Deus-Neumann B, Zenk MH (1999). "Biosynthesis of Erythrina alkaloids in Erythrina crista-galli". Phytochemistry. 52 (3): 373–82. PMID 10501023.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Barton, D. H. R.; Boar, R. B.; Widdowson, D. A. J. Chem. Soc. C 1970, 1208
- ^ M. F. Grundon (1 January 1979). The Alkaloids:. Royal Society of Chemistry. pp. 16–. ISBN 978-0-85186-660-4.
Further Reading
- Soto-Hernández, R. Marcos, et al. "Erythrina, a Potential Source of Chemicals from the Neotropics." Bioactive Compounds in Phytomedicine (2011): 163.
- Chou, Chun Tzer, and John S. Swenton. "A convergent strategy for synthesis of Erythrina alkaloids." Journal of the American Chemical Society 109.22 (1987): 6898-6899.
- Castedo, Luis, and Domingo Dominguez. "Dibenzazonine Alkaloids." The Alkaloids: Chemistry and Pharmacology 35 (1989): 177-214.