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

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-c...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of the American Chemical Society 2018-08, Vol.140 (30), p.9502-9511
Hauptverfasser: Zou, Yike, Li, Xiangqin, Yang, Yun, Berritt, Simon, Melvin, Jason, Gonzales, Stephen, Spafford, Matthew, Smith, Amos B
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung: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.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.8b04053