Total synthesis of bafilomycin A1 |
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Authors: | Kleinbeck Florian Fettes Gabriela J Fader Lee D Carreira Erick M |
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Institution: | ETH Zürich HCI H335, Wolfgang-Pauli-Strasse 10, 8093 Zürich, Switzerland. |
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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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