Total synthesis of bafilomycin A1

F Kleinbeck, GJ Fettes, LD Fader…

Index: Kleinbeck, Florian; Fettes, Gabriela J.; Fader, Lee D.; Carreira, Erick M. Chemistry - A European Journal, 2012 , vol. 18, # 12 p. 3598 - 3610

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Citation Number: 9

Abstract

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- ...