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Light-driven Molecular Motors on Surfaces for Single Molecular Imaging
Published on: March 13, 2019
Microfluidic light-driven synthesis of tetracyclic molecular architectures
Javier Mateos1, Nicholas Meneghini1, Marcella Bonchio1
1Dipartimento di Scienze Chimiche and ITM-CNR UoS of Padova, Università di Padova, Via Marzolo 1, 35131 Padova, Italy.
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.
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