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Microfluidic light-driven synthesis of tetracyclic molecular architectures.


ABSTRACT: Herein we report an effective synthetic method for the direct assembly of highly functionalized tetracyclic pharmacophoric cores. Coumarins and chromones undergo diastereoselective [4 + 2] cycloaddition reactions with light-generated photoenol intermediates. The reactions occur by aid of a microfluidic photoreactor (MFP) in high yield (up to >98%) and virtually complete diastereocontrol (>20:1 dr). The method is easily scaled-up to a parallel setup, furnishing 948 mg of product over a 14 h reaction time. Finally, a series of manipulations of the tetracyclic scaffold obtained gave access to valuable precursors of biologically active molecules.

SUBMITTER: Mateos J 

PROVIDER: S-EPMC6176812 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Microfluidic light-driven synthesis of tetracyclic molecular architectures.

Mateos Javier J   Meneghini Nicholas N   Bonchio Marcella M   Marino Nadia N   Carofiglio Tommaso T   Companyó Xavier X   Dell'Amico Luca L  

Beilstein journal of organic chemistry 20180917


Herein we report an effective synthetic method for the direct assembly of highly functionalized tetracyclic pharmacophoric cores. Coumarins and chromones undergo diastereoselective [4 + 2] cycloaddition reactions with light-generated photoenol intermediates. The reactions occur by aid of a microfluidic photoreactor (MFP) in high yield (up to >98%) and virtually complete diastereocontrol (>20:1 dr). The method is easily scaled-up to a parallel setup, furnishing 948 mg of product over a 14 h react  ...[more]

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