PubAg

Main content area

Total Synthesis of (−)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy

Author:
Zou, Yike, Li, Xiangqin, Yang, Yun, Berritt, Simon, Melvin, Jason, Gonzales, Stephen, Spafford, Matthew, Smith, Amos B.
Source:
Journal of the American Chemical Society 2018 v.140 no.30 pp. 9502-9511
ISSN:
1520-5126
Subject:
alkylation, aromatic compounds, catalytic activity, cross-coupling reactions, cyclization reactions, diastereoselectivity, palladium
Abstract:
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.
Agid:
6079129