Stone, Steven D.Lajkiewicz, Neil J.Whitesell, LukeHilmy, AhmedPorco, John A.2018-01-292018-01-292014-12-07Steven D Stone, Neil J Lajkiewicz, Luke Whitesell, Ahmed Hilmy, John A Porco. 2015. "Biomimetic kinetic resolution: highly enantio- and diastereoselective transfer hydrogenation of aglain ketones to access flavagline natural products.." J Am Chem Soc, Volume 137, Issue 1, pp. 525 - 530.1520-5126https://hdl.handle.net/2144/26456We have previously reported asymmetric syntheses and absolute configuration assignments of the aglains (+)-ponapensin and (+)-elliptifoline and proposed a biosynthetic kinetic resolution process to produce enantiomeric rocaglamides and aglains. Herein, we report a biomimetic approach for the synthesis of enantiomerically enriched aglains and rocaglamides via kinetic resolution of a bridged ketone utilizing enantioselective transfer hydrogenation. The methodology has been employed to synthesize and confirm the absolute stereochemistries of the pyrimidone rocaglamides (+)-aglaiastatin and (-)-aglaroxin C. Additionally, the enantiomers and racemate of each metabolite were assayed for inhibition of the heat-shock response, cytotoxicity, and translation inhibition.p. 525 - 530This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html), which permits copying and redistribution of the article or any adaptations for non-commercial purposes.ChemistryAsymmetric transfer hydrogenationRocaglamide derivativesEnantioselectivityElliptifoliaInhibitorsBenzofuransBiological productsBiomimetic materialsCrystallography, X-rayHeterocyclic compounds, 3-ringHydrogenationKetonesKineticsModels, molecularMolecular structurePyrrolesQuantum theoryStereoisomerismChemical sciencesArticle10.1021/ja511728b