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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
The Stereoselective Total Synthesis of the Elusive Cephalosporolide F
Leonardo Xochicale-Santana1,2, Omar Cortezano-Arellano3, Bernardo A Frontana-Uribe4,5
1Centro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP), 14 Sur Esq. San Claudio, Col. San Manuel, 72570 Puebla, México.
Abstract:
Here we report a seven-step protecting-group-free stereoselective total synthesis of the elusive (+)-cephalosporolide F from d-glucose. A microwave-assisted reaction between the Meldrum's acid and the d-glucose to the respective octono-1,4-lactone derivative, and a low temperature visible-light photoredox spirocyclization of a chiral N-alkoxyphthalimide to ceph F, are the two key chemical reactions that allowed the accomplishment of this unprecedented feat under an environmentally friendly processes.
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