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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Asymmetric Divergent Synthesis of Miophytocen D, Roridin E, Verrucarin J, and Verrucarol
Zhang-Qin Xue1, Feng-Sheng Jiang1, Wen-Kai Ge1
1State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, Key Laboratory of Chemical Biology (Ministry of Education), Shandong Basic Science Special Academic Zone (Pharmacy), Shandong University, Jinan250012, P. R. China.
Abstract:
Herein, we report a divergent asymmetric synthesis of miophytocen D, roridin E, verrucarin J, and verrucarol. The synthesis features an exo-selective Diels-Alder cycloaddition, a biomimetic chemoselective oxacyclization for tetrahydropyran ring assembly, a conformation-controlled alkene-epoxy cyclization to access divergent molecular scaffolds, and a modular ring-closing metathesis (RCM)-based macrocyclization. This study delivers the first total synthesis of miophytocen D, furnishes hundred-milligram-scale access to verrucarol, and provides chemical support for the proposed biosynthetic transformation.
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