Catalytic Dearomatization Approach to Quinolizidine Alkaloids: Five Step Total Synthesis of (±)-Lasubine II

Catalytic Dearomatization Approach to Quinolizidine Alkaloids: Five Step Total Synthesis of (±)-Lasubine II

A series of high-yielding silver­(I)-catalyzed cyclization reactions of pyridine-, isoquinoline-, and pyrazine-ynones are described. The operationally simple and mild reaction conditions are a significant improvement over previously reported thermal cyclizations. The quinolizinone products were also...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2016-12, Vol.18 (24), p.6256-6259
Hauptverfasser: James, Michael J, Grant, Niall D, O’Brien, Peter, Taylor, Richard J. K, Unsworth, William P
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:A series of high-yielding silver­(I)-catalyzed cyclization reactions of pyridine-, isoquinoline-, and pyrazine-ynones are described. The operationally simple and mild reaction conditions are a significant improvement over previously reported thermal cyclizations. The quinolizinone products were also used in a novel dearomatization strategy to prepare 0.53 g of the alkaloid lasubine II in five steps and 36% overall yield.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03017