Additionally, we were joined much later on by one of the most talented post docs (@Griffin__Barnes) I’ve ever met! He helped us push massive scale reactions, and has been a wellspring of chemical wisdom since joining!
Very proud to have been part of this work! A few months into the project, I was joined by a venerable graduate student (@maithiliterpene) who came up with and carried out the beautiful halogen dance sequence showcased in our synthesis!
TEN STEPS TO A MARINE TREASURE: Gram-Scale Synthesis of Bipinnatin J – featuring methods that weren't known ≅3 years ago to forge 3 key C–C bonds... Appearing today in @ChemRxiv (https://t.co/AVocmrW1zJ).
Quick Summary: A concise, scalable total synthesis of (–)-Bipinnatin J is disclosed. Commencing from inexpensive starting materials, this marine diterpenoid was fashioned through a highly convergent synthesis enabled by two Ni-electrocatalytic decarboxylative cross–couplings (DCC) leveraging succinate as an ethylene 2-carbon bridge, a unique halogen dance- Zweifel sequence to rapidly access a trisubstituted furan, a recently disclosed Ni-catalyzed 1,6-conjugate addition, and an asymmetric proton transfer.
Shout out to the team that made it happen: @tonyjohn07@griffin__barnes@maithiliterpene
TEN STEPS TO A MARINE TREASURE: Gram-Scale Synthesis of Bipinnatin J – featuring methods that weren't known ≅3 years ago to forge 3 key C–C bonds... Appearing today in @ChemRxiv (https://t.co/AVocmrW1zJ).
Quick Summary: A concise, scalable total synthesis of (–)-Bipinnatin J is disclosed. Commencing from inexpensive starting materials, this marine diterpenoid was fashioned through a highly convergent synthesis enabled by two Ni-electrocatalytic decarboxylative cross–couplings (DCC) leveraging succinate as an ethylene 2-carbon bridge, a unique halogen dance- Zweifel sequence to rapidly access a trisubstituted furan, a recently disclosed Ni-catalyzed 1,6-conjugate addition, and an asymmetric proton transfer.
Shout out to the team that made it happen: @tonyjohn07@griffin__barnes@maithiliterpene