Ferrugine

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 $[α]_{D}^{19} = + 55$ ° (CHCl₃).^[2]

References

↑ "Ferrugine. Novel tropane alkaloid". Chemistry & Industry (London, United Kingdom) (18): 794. 1975. .
↑ ^2.0 ^2.1 "Alkaloids of Darlingia ferruginea". Australian Journal of Chemistry 32 (11): 2537. 1979. doi:10.1071/CH9792537.
↑ "Thermal elimination of diethyldithiocarbamates and application in the synthesis of (+/-)-ferrugine". The Journal of Organic Chemistry 73 (20): 8116–8119. October 2008. 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.
↑ "Approaches to the enantioselective synthesis of ferrugine and its analogues.". Tetrahedron 68 (39): 8236–8244. September 2012. doi:10.1016/j.tet.2012.07.061.

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[1] "Ferrugine. Novel tropane alkaloid". Chemistry & Industry (London, United Kingdom) (18): 794. 1975. .

[Bick_1979-2] 2.0 ^2.1 "Alkaloids of Darlingia ferruginea". Australian Journal of Chemistry 32 (11): 2537. 1979. doi:10.1071/CH9792537.

[3] "Thermal elimination of diethyldithiocarbamates and application in the synthesis of (+/-)-ferrugine". The Journal of Organic Chemistry 73 (20): 8116–8119. October 2008. doi:10.1021/jo801652x. PMID 18785775.

[4] Ahmed S (August 2009). Total synthesis of ferrugine and synthetic studies towards ferrugine and stemofoline (Ph.D. thesis). University of Birmingham.

[5] "Approaches to the enantioselective synthesis of ferrugine and its analogues.". Tetrahedron 68 (39): 8236–8244. September 2012. doi:10.1016/j.tet.2012.07.061.

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v t e Alkaloid groups
Indole	5-MeO-DMT Alstonine Dimethyltryptamine Harmala alkaloids Psilocin Psilocybin Reserpine Serotonin Tryptamine Yohimbine
Phenethylamine	Amphetamine Cathinone Dopamine Ephedrine Mescaline Methamphetamine Phenethylamine Tyramine
Purine	Caffeine Theobromine Theophylline
Pyridine	Coniine
Pyrrolidine	Nicotine
Quinoline	Quinine
Isoquinoline	Codeine Morphine
Tropane	Atropine Cocaine Hyoscyamine Scopolamine
Terpenoid	Aconitine Solanine
Betaines	Choline Muscarine

Ferrugine

Topic: Chemistry

See also

References