10-Step, Gram-Scale Total Synthesis of (−)-Bipinnatin J

Abstract

A concise, scalable total synthesis of (−)-bipinnatin J is disclosed. Commencing from inexpensive starting materials, this marine diterpenoid was fashioned through a convergent synthesis enabled by Ni-electrocatalytic decarboxylative cross–coupling taking advantage of succinate as an ethylene 2-carbon bridge, a unique halogen dance-Zweifel sequence to access a trisubstituted furan, a Ni-mediated 1,6-conjugate addition, and an asymmetric proton transfer.