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DOI: 10.1055/s-0037-161114
Enantioselective Synthesis of 4-Amino-3-hydroxybenzopyran Flavanol Derivatives from Chalcones
Funding was provided by the UIC Department of Chemistry.Publication History
Received: 05 October 2018
Accepted after revision: 12 October 2018
Publication Date:
21 November 2018 (online)
Abstract
A concise method that is easily amenable for analogue synthesis has been developed to enantioselectively access 4-amino-3-hydroxybenzopyrans from chalcones. Epoxy alcohols were formed from chalcones through a Corey–Bakshi–Shibata reduction of the enone and subsequent Sharpless asymmetric epoxidation of the allylic alcohol. The epoxy alcohols were protected, regioselectively opened with various amines using catalytic europium(III) triflate, and the resulting free alcohols were orthogonally protected. Concomitant deprotection and intramolecular nucleophilic aromatic substitution provided the benzopyran core, which is poised to undergo additional reactions to provide a diverse chemical library with ideal properties for biological evaluation.
Key words
natural products - stereoselective synthesis - medicinal chemistry - nucleophilic aromatic substitution - nitrogen - heterocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-161114.
- Supporting Information
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