10-Step, Gram-Scale Total Synthesis of (−)-Bipinnatin J
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.
Authors
- Maithili Pokle (ORCID: https://orcid.org/0009-0004-0412-0584)
- Anthony J. Rodriguez
- Phil S. Baran (ORCID: https://orcid.org/0000-0001-9193-9053)
- Gary Barnes
Institutions
- Scripps Institution of Oceanography (US)
- Scripps (United States) (US)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2025-05-06
- DOI
- https://doi.org/10.1021/jacs.5c04761
- Citations
- 4
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- George E. Hewitt Foundation for Medical Research
- National Institute of General Medical Sciences