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Synthesis of the C29−C37 Bicyclic Ether Core of (+)-Sorangicin A

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journal contribution
posted on 14.09.2006, 00:00 by Michael T. Crimmins, Matthew W. Haley
Construction of the unique bicyclic bis-ether core of the macrolide (+)-sorangicin A has been achieved. This fragment was prepared by utilizing a one-pot cascade of three bond forming events. An epoxide opening of the epoxy tosylate 2 led to the formation of the tetrahydropyran and subsequently to a second epoxide. Finally, a second epoxide opening closed the tetrahydrofuran ring. The bicyclic fragment was synthesized in just nine steps from (E)-cinnamaldehyde.

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