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.
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Titolo: | Microfluidic light-driven synthesis of tetracyclic molecular architectures |
Autori: | |
Data di pubblicazione: | 2018 |
Rivista: | |
Handle: | http://hdl.handle.net/20.500.11770/298895 |
Appare nelle tipologie: | 1.1 Articolo in rivista |