Uvaricin

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]

(+)-Uvaricin
Names
Preferred IUPAC name
(1S)-1-[(2R,2′R,5R,5′R)-5′-{(1R)-1-Hydroxy-13-[(5S)-5-methyl-2-oxo-2,5-dihydrofuran-3-yl]tridecyl}[2,2′-bioxolan]-5-yl]undecyl acetate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C39H68O7/c1-4-5-6-7-8-15-18-21-24-35(44-31(3)40)36-27-28-38(46-36)37-26-25-34(45-37)33(41)23-20-17-14-12-10-9-11-13-16-19-22-32-29-30(2)43-39(32)42/h29-30,33-38,41H,4-28H2,1-3H3/t30-,33+,34+,35-,36+,37+,38+/m0/s1 checkY
    Key: JQOYPOSGHDJFLI-AVNCTIOFSA-N checkY
  • O=C\1O[C@H](/C=C/1CCCCCCCCCCCC[C@@H](O)[C@@H]3O[C@@H]([C@@H]2O[C@H](CC2)[C@@H](OC(=O)C)CCCCCCCCCC)CC3)C
Properties
C39H68O7
Molar mass 648.966 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Jolad, S. D.; Hoffmann, J. J.; Schram, K. H.; Cole, J. R.; Tempesta, M. S.; Kriek, G. R.; Bates, R. B. (1982). "Uvaricin, a New Antitumor Agent from Uvaria accuminata (Annonaceae)". Journal of Organic Chemistry. 47 (16): 3151–3153. doi:10.1021/jo00137a024.
  2. Zafra-Polo, M. C.; González, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D. (1996). "Acetogenins from Annonaceae, Inhibitors of Mitochondrial Complex I". Phytochemistry. 42 (2): 253–271. doi:10.1016/0031-9422(95)00836-5. PMID 8688168.
  3. Yazbak, A.; Sinha, S. C.; Keinan, E. (1998). "Total Synthesis of Uvaricin" (PDF). Journal of Organic Chemistry. 63 (17): 5863–5868. doi:10.1021/jo980453a. PMID 11672188. Archived from the original (PDF) on 2011-07-17. Retrieved 2008-07-14.
  4. Burke, S. D.; Jiang, L. (2001). "Formal Synthesis of Uvaricin via Palladium-Mediated Double Cyclization". Organic Letters. 3 (12): 1953–1956. doi:10.1021/ol0160304. PMID 11405753.


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