1379802-76-2Relevant academic research and scientific papers
Total synthesis of bafilomycin A1
Kleinbeck, Florian,Fettes, Gabriela J.,Fader, Lee D.,Carreira, Erick M.
, p. 3598 - 3610 (2012/05/04)
A convergent synthesis of bafilomycin A1, 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. Copyright
