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Total Synthesis of (−)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy
- Zou, Yike, Li, Xiangqin, Yang, Yun, Berritt, Simon, Melvin, Jason, Gonzales, Stephen, Spafford, Matthew, Smith, Amos B.
- Journal of the American Chemical Society 2018 v.140 no.30 pp. 9502-9511
- alkylation, aromatic compounds, catalytic activity, cross-coupling reactions, cyclization reactions, diastereoselectivity, palladium
- A unified synthetic strategy leading to the total synthesis of (−)-nodulisporic acids D, C, and B is described. Key synthetic transformations include a nickel–chromium-mediated cyclization, an aromatic ring functionalization employing a novel copper-promoted alkylation, a palladium-catalyzed cross-coupling cascade/indole ring construction, and a palladium-mediated regio- and diastereoselective allylic substitution/cyclization reaction, the latter to construct ring D.