Uvaricin Explained

Uvaricin is a bis(tetrahydrofuranoid) fatty acid lactone that was first isolated in 1982 from the roots of the Annonaceae Uvaria acuminata.^[1] Uvaricin was the first known example in a class of compounds known as acetogenins. Acetogenins, which are found in plants of the family Annonaceae, seem to kill cells by inhibiting NADH dehydrogenase in the mitochondrion.^[2] A method to synthesize uvaricin was first published in 1998,^[3] and an improved stereoselective synthesis published in 2001.^[4]

Notes and References

1. Jolad, S. D. . Hoffmann, J. J. . Schram, K. H. . Cole, J. R. . Tempesta, M. S. . Kriek, G. R. . Bates, R. B. . Uvaricin, a New Antitumor Agent from Uvaria accuminata (Annonaceae) . Journal of Organic Chemistry . 1982 . 47 . 16 . 3151–3153 . 10.1021/jo00137a024 .
2. Zafra-Polo, M. C. . González, M. C. . Estornell, E. . Sahpaz, S. . Cortes, D. . Acetogenins from Annonaceae, Inhibitors of Mitochondrial Complex I . . 1996 . 42 . 2 . 253–271 . 10.1016/0031-9422(95)00836-5 . 8688168 . 1996PChem..42..253Z .
3. Yazbak, A. . Sinha, S. C. . Keinan, E. . Total Synthesis of Uvaricin . Journal of Organic Chemistry . 1998 . 63 . 17 . 5863–5868 . 10.1021/jo980453a . 11672188 . 2008-07-14 . https://web.archive.org/web/20110717211654/http://www.technion.ac.il/~keinanj/pub/92.pdf . 2011-07-17 . dead .
4. Burke, S. D. . Jiang, L. . Formal Synthesis of Uvaricin via Palladium-Mediated Double Cyclization . Organic Letters . 2001 . 3 . 12 . 1953–1956 . 10.1021/ol0160304 . 11405753 .