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10-Step, Gram-Scale Total Synthesis of (-)-Bipinnatin J
Anthony J Rodriguez1, Maithili S Pokle1, Griffin L Barnes1
1Department of Chemistry, Scripps Research, La Jolla, California 92037, United States.
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.
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