A concise and modular synthesis of pyranicin

Abstract

(Chemical Equation Presented) A modular, 13-step synthesis of the tetrahydropyran-containing annonaceous acetogenin pyranicin is reported. Key features are the use of an Achmatowicz oxidation - Kishi reduction sequence for the assembly of a pyranone from a furan and the application of Fu's alkyl - alkyl Suzuki coupling for subunit union. © 2008 American Chemical Society.