Ferrugine
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| Formula | C15H19NO |
| Molar mass | 229.323 g·mol−1 |
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Ferrugine (2α-benzoyltropane) is a tropane alkaloid discovered in the basic extract of the Australian rainforest tree Darlingia ferruginea where it occurs in the leaves and stems. The structure has been determined through spectroscopic analysis[1][2] and confirmed by chemical synthesis.[3][4][5]
(+)-Ferrugine is the natural enantiomer, with a reported specific rotation of ° (CHCl3).[2]
![{\displaystyle [\alpha ]_{D}^{19}=+55}](https://wikimedia.org/api/rest_v1/media/math/render/svg/56fb765f3de5100f9d3fbed7e3b425e443028d56)
See also
[edit]References
[edit]- ↑ Bick IC, Gillard JW, Woodruff M (1975). "Ferrugine. Novel tropane alkaloid". Chemistry & Industry (18). London, United Kingdom: 794..
- 1 2 Bick I, Gillard J, Leow H (1979). "Alkaloids of Darlingia ferruginea". Australian Journal of Chemistry. 32 (11): 2537. doi:10.1071/CH9792537.
- ↑ Ahmed S, Baker LA, Grainger RS, Innocenti P, Quevedo CE (October 2008). "Thermal elimination of diethyldithiocarbamates and application in the synthesis of (+/-)-ferrugine". The Journal of Organic Chemistry. 73 (20): 8116–8119. doi:10.1021/jo801652x. PMID 18785775.
- ↑ Ahmed S (August 2009). Total synthesis of ferrugine and synthetic studies towards ferrugine and stemofoline (Ph.D. thesis). University of Birmingham.
- ↑ Lazny R, Sienkiewicz M, Olenski T, Urbanczyk-Lipkowska Z, Kalicki P (September 2012). "Approaches to the enantioselective synthesis of ferrugine and its analogues". Tetrahedron. 68 (39): 8236–8244. doi:10.1016/j.tet.2012.07.061.
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