Total Synthesis of (-)-Fasicularin.

J Org Chem

Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.

Published: August 2024

Asymmetric total synthesis of (-)-fasicularin was achieved in nine steps from a commercially available inexpensive material, by leveraging (1) an aryl radical-mediated, copper-catalyzed Sonogashira-type cross-coupling, (2) a Au-catalyzed tandem intramolecular alkyne hydroamination/iminium formation/intramolecular allylation, and (3) a tandem hydrogenation/hydrogenolysis/intramolecular reductive amination as key transformations.

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http://dx.doi.org/10.1021/acs.joc.4c01447DOI Listing

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