rocaglamide

{{jargon|date=January 2025}}

{{Chembox

| ImageFile = Rocaglamide.svg

| ImageSize =200 px

| ImageAlt =

| PIN =(1R,2R,3S,3aR,8bS)-1,8b-Dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide

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|Section1={{Chembox Identifiers

| CASNo =84573-16-0

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = FRG4N852F7

| PubChem =331783

| SMILES = CN(C)C(=O)[C@@H]1[C@H]([C@]2([C@@]([C@@H]1O)(C3=C(C=C(C=C3O2)OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5

| ChemSpiderID = 293974

| InChI = 1/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1

| InChIKey = DAPAQENNNINUPW-IDAMAFBJBD

| StdInChI = 1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1

| StdInChIKey = DAPAQENNNINUPW-IDAMAFBJSA-N

}}

|Section2={{Chembox Properties

| C=29 | H=31 | N=1 | O=7

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|Section3={{Chembox Hazards

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Rocaglamide is a natural product which belongs to a class of molecules called flavaglines.{{cite book | vauthors = Ebada SS, Lajkiewicz N, Porco JA, Li-Weber M, Proksch P | chapter=Chemistry and Biology of Rocaglamides (= Flavaglines) and Related Derivatives from Aglaia Species (Meliaceae) | title = Progress in the Chemistry of Organic Natural Products Vol. 94 | journal = Progress in the Chemistry of Organic Natural Products |series = Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products| volume = 94 | pages = 1–58 | year = 2011 | pmid = 21833837 | doi = 10.1007/978-3-7091-0748-5_1 | isbn = 978-3-7091-0747-8 | pmc = 4157394 }}{{cite journal | vauthors = Ribeiro N, Thuaud F, Nebigil C, Désaubry L | title = Recent advances in the biology and chemistry of the flavaglines | journal = Bioorganic & Medicinal Chemistry | volume = 20 | issue = 6 | pages = 1857–64 | date = March 2012 | pmid = 22071525 | doi = 10.1016/j.bmc.2011.10.048 }} This compound was isolated in 1982 by Ming-Lu King (金明儒) and colleagues based on its antileukemic activity.{{cite journal | vauthors = King ML, Chiang CC, Ling HC, Fujita E, Ochiai M, McPhail AT |title=X-Ray crystal structure of rocaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran from Aglaia elliptifolia |journal=Chem. Commun. |issue= 20|pages=1150–1 |year=1992 |doi=10.1039/c39820001150}} The name of Rocaglamide is named from two parts: Roc- and aglamide. Roc- means Republic of China (中華民國), where this product was first isolated; aglamide indicates this product is isolated from Large-leaved Aglaia (Scientific name: Aglaia rimosa{{ Cite web |url =https://powo.science.kew.org/taxon/urn:lsid:ipni.org:names:577291-1|title =Aglaia rimosa (Blanco) Merr.|publisher = Plants of the World Online|language = en|accessdate = 2022-12-14}}). Like other flavaglines, rocaglamide displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities. Rocaglamide A (RocA) inhibits eukaryotic translation initiation by binding to the translation initiation factor eIF4A and converting it into a translational repressor.{{cite journal | vauthors = Iwasaki S, Floor SN, Ingolia NT | title = Rocaglates convert DEAD-box protein eIF4A into a sequence-selective translational repressor | journal = Nature | volume = 534 | issue = 7608 | pages = 558–61 | date = June 2016 | pmid = 27309803 | doi = 10.1038/nature17978 | pmc=4946961| bibcode = 2016Natur.534..558I }}

Rocaglamide was first synthesized by Barry Trost in 1990.{{cite journal | vauthors = Trost BM, Greenspan PD, Yang BV, Saulnier MG |title=An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of (−)-rocaglamide |journal= Journal of the American Chemical Society |volume=112 |issue=24 |pages=9022–4 |date=November 1990 |doi=10.1021/ja00180a081 |bibcode=1990JAChS.112.9022T }} Although other syntheses have been described since, Trost’s remains the only one to afford rocaglamide in an enantio-specific manner.