Rocaglamide
 | |
| Names | |
|---|---|
| IUPAC name
(1R,2R,3S,3aR,8bS)-1,8b-Dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide | |
| Identifiers | |
| 84573-16-0 | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 293974 |
| PubChem | 331783 |
| |
| |
| Properties | |
| C29H31NO7 | |
| Molar mass | 505.57 g·mol−1 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Rocaglamide is a natural product which belongs to a class of molecules called flavaglines.[1][2] This compound was isolated in 1982 by King and colleagues based on its antileukemic activity.[3] Like other flavaglines, rocaglamide displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities.
Rocaglamide was first synthesized by Barry Trost in 1990.[4] Although other syntheses have been described since, Trost’s remains the only one to afford rocaglamide in an enantio-specific manner.
See also
References
- ↑ Ebada SS, Lajkiewicz N, Porco JA, Li-Weber M, Proksch P (2011). "Chemistry and biology of rocaglamides (= flavaglines) and related derivatives from aglaia species (meliaceae)". Fortschr Chem Org Naturst. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. 94: 1–58. doi:10.1007/978-3-7091-0748-5_1. ISBN 978-3-7091-0747-8. PMID 21833837.
- ↑ Ribeiro N, Thuaud F, Nebigil C, Désaubry L (March 2012). "Recent advances in the biology and chemistry of the flavaglines". Bioorg. Med. Chem. 20 (6): 1857–64. doi:10.1016/j.bmc.2011.10.048. PMID 22071525.
- ↑ King M.L.; Chiang C.C.; Ling H.C.; Fujita E.; Ochiai M.; McPhail A.T. (1992). "X-Ray crystal structure of rocaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran from Aglaia elliptifolia". Chem. Commun.: 1150–1. doi:10.1039/c39820001150.
- ↑ Trost, B.M., Greenspan, P.D., Yang, B.V., Saulnier M.G. (November 1990). "An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of (−)-rocaglamide". J. Am. Chem. Soc. 112 (24): 9022–4. doi:10.1021/ja00180a081.
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