Total Synthesis of an Anti-Helicobacter pylori Agent, Actinopyrone A

Actinopyrone A, an anti‐Helicobacter pylori agent, was synthesized in nine steps from a silyl dienol ether. A vinylogous anti‐aldol was stereoselectively synthesized by our developed remote stereoinduction methodology; coupling of this with a sulfone and a phosphonate species led to the construction of a vinylpyrone compound. This was submitted to reductive de‐conjugation to give actinopyrone A. The absolute stereochemistry of actinopyrone A was determined to have the configuration 14R,15R. Join and kick out! Actinopyrone A, an anti‐Helicobacter pylori agent, was synthesized in nine steps by the connection of four components. This synthesis features stereoselective construction of the side chain by remote stereoinduction methodology and reductive de‐conjugation of vinylpyrone to an allylpyrone moiety.