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    Biomimetic kinetic resolution: highly enantio- and diastereoselective transfer hydrogenation of aglain ketones to access flavagline natural products

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    Date Issued
    2014-12-07
    Publisher Version
    10.1021/ja511728b
    Author(s)
    Stone, Steven D.
    Lajkiewicz, Neil J.
    Whitesell, Luke
    Hilmy, Ahmed
    Porco, John A.
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    Permanent Link
    https://hdl.handle.net/2144/26456
    Citation (published version)
    Steven 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.
    Abstract
    We 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.
    Rights
    This 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.
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    • BU Open Access Articles [3664]
    • CAS: Chemistry: Scholarly Papers [120]


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