Xinyue Chen, Danyang Zhang, Dan Xu, Huan Zhou, Gong Xu.Remote C-H Activation Strategy Enables Total Syntheses of Nortriterpenoids (±)-Walsucochin B and (±)-Walsucochinoids M and N

Remote C-H Activation Strategy Enables Total Syntheses of Nortriterpenoids (±)-Walsucochin B and (±)-Walsucochinoids M and N

Xinyue Chen, Danyang Zhang, Dan Xu, Huan Zhou, Gong Xu

Organic Letters

DOI:10.1021/acs.orglett.0c02548

Abstract

Total syntheses of (±)-walsucochin B and (±)-walsucochinoids M and N have been achieved from farnesyl bromide. The key steps of the synthetic sequence are the titanocene-mediated radical cyclization and base-induced cycloaromatization for the rapid construction of the 6/6/5/6-fused tetracyclic skeleton. Importantly, a Cu-mediated remote C-H hydroxylation reaction has been developed to site-selectively install the oxygen function at the C-7 position of the target molecules, thus solving the biggest challenge for the synthesis of the compounds.