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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]

PMID: 30344766

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