{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = (+)-Ferrugine | image = Ferrugine v2.svg | width = 150px | caption =
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<!-- Identifiers --> | CAS_number = 58471-11-7 | CAS_supplemental = | PubChem = 102489592 | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 127384569 | UNII = | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms =
<!--Chemical data--> | IUPAC_name = (8-methyl-8-azabicyclo[3.2.1]octan-2-yl)-phenylmethanone | C=15 | H=19 | N=1 | O=1 | SMILES = C(=O)([C@@H]1[C@]2(N(C)[C@@](CC1)(CC2)[H])[H])C3=CC=CC=C3 | StdInChI = 1S/C15H19NO/c1-16-12-7-9-13(14(16)10-8-12)15(17)11-5-3-2-4-6-11/h2-6,12-14H,7-10H2,1H3/t12-,13-,14-/m0/s1 | StdInChIKey = FKBXXVPBVMWIDS-IHRRRGAJSA-N }}
'''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<ref>{{cite journal | vauthors = Bick IC, Gillard JW, Woodruff M | title = Ferrugine. Novel tropane alkaloid | journal = Chemistry & Industry | location = London, United Kingdom | issue = 18 | pages = 794 | date = 1975 }}.</ref><ref name = "Bick_1979">{{cite journal | vauthors = Bick I, Gillard J, Leow H | title = Alkaloids of Darlingia ferruginea | journal = Australian Journal of Chemistry | volume = 32 | issue = 11 | pages = 2537 | date = 1979 | doi = 10.1071/CH9792537 }}</ref> and confirmed by chemical synthesis.<ref>{{cite journal | vauthors = Ahmed S, Baker LA, Grainger RS, Innocenti P, Quevedo CE | title = Thermal elimination of diethyldithiocarbamates and application in the synthesis of (+/-)-ferrugine | journal = The Journal of Organic Chemistry | volume = 73 | issue = 20 | pages = 8116–8119 | date = October 2008 | pmid = 18785775 | doi = 10.1021/jo801652x }}</ref><ref>{{cite thesis | vauthors = Ahmed S | date = August 2009 | title = Total synthesis of ferrugine and synthetic studies towards ferrugine and stemofoline | degree = Ph.D. | publisher = University of Birmingham | url = https://etheses.bham.ac.uk/id/eprint/1281/ }}</ref><ref>{{cite journal | vauthors = Lazny R, Sienkiewicz M, Olenski T, Urbanczyk-Lipkowska Z, Kalicki P | title = Approaches to the enantioselective synthesis of ferrugine and its analogues. | journal = Tetrahedron | date = September 2012 | volume = 68 | issue = 39 | pages = 8236–8244 | doi = 10.1016/j.tet.2012.07.061 }}</ref>
(+)-Ferrugine is the natural enantiomer, with a reported specific rotation of <math>[\alpha]_D^{19} = +55</math>° (CHCl<sub>3</sub>).<ref name = "Bick_1979" />
== See also == * Ferruginine
== References == {{reflist}}
{{Alkaloids}}
{{Organic-compound-stub}}
Category:Alkaloids Category:Tropanes Category:Benzaldehydes