Total synthesis of bafilomycin A1

Chemistry : a European Journal
Florian KleinbeckErick M Carreira

Abstract

A convergent synthesis of bafilomycin A(1), a potent inhibitor of V-type ATPases, is presented. The synthesis relies on the zinc triflate mediated diastereoselective addition of a complex enyne to a sensitive aldehyde as the key fragment coupling. A ruthenium-catalyzed trans-reduction of the resulting propargylic enyne efficiently installs the required C10-C13 trans,trans-diene subunit, implementing an alternative strategy to traditional palladium-catalyzed cross-coupling strategies. A highly selective oxidation of a secondary hydroxyl group in a triol sets the stage for the completion of the synthesis.

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Citations

Oct 16, 2015·Proceedings of the Japan Academy. Series B, Physical and Biological Sciences·Ei-Ichi Negishi, Shiqing Xu
Apr 14, 2016·Organic Letters·Yusuke OguraShigefumi Kuwahara
Oct 24, 2014·Organic & Biomolecular Chemistry·Balla ChandrasekharSubhash Ghosh
Feb 12, 2019·Chemistry : a European Journal·Friederike RatschHans-Günther Schmalz
Apr 20, 2021·The Journal of Organic Chemistry·Arun K Ghosh, Che-Sheng Hsu
May 7, 2019·Organic Letters·Taejung KimYoko Saikawa

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