Total Synthesis of (-)-Phomoarcherin C

J Org Chem. 2019 Nov 1;84(21):14053-14060. doi: 10.1021/acs.joc.9b02206. Epub 2019 Oct 24.

Abstract

A full account on the first total synthesis of a chroman meroterpenoid, (-)-phomoarcherin C, has been described. Key synthetic transformations include phenyl boronic acid-mediated 6π-electrocyclization reaction, a stereospecific hydrogenation driven by thermodynamic conformational stability of the product, and regioselective formylation. The strategy employed is considerably short, is atom-economical, and can open the doors to provide access to various other natural products of the same kind.