Catalytic Asymmetric Formal Total Synthesis of (−)-Triptophenolide and (+)-Triptolide

Catalytic Asymmetric Formal Total Synthesis of (−)-Triptophenolide and (+)-Triptolide

Catalytic asymmetric formal synthesis of (−)-Triptophenolide and (+)-Triptolide have been achieved. Key reaction involves Palladium catalyzed asymmetric conjugate addition of aryl boronic acid to 3-methyl cyclohexe-1-none to form quaternary carbon. Claisen rearrangement and subsequent aldol reaction...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Natural products and bioprospecting 2016-06, Vol.6 (3), p.183-186
Hauptverfasser: Xu, Wen-Dan, Li, Liang-Qun, Li, Ming-Ming, Geng, Hui-Chun, Qin, Hong-Bo
Format: Artikel
Sprache:eng
Schlagworte:
Biomedical and Life Sciences
Bioorganic Chemistry
carbon
catalytic activity
chemical reactions
Food Science
Life Sciences
Medicinal Chemistry
palladium
Pharmacology/Toxicology
Plant Biochemistry
Plant Sciences
Short Communication
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Catalytic asymmetric formal synthesis of (−)-Triptophenolide and (+)-Triptolide have been achieved. Key reaction involves Palladium catalyzed asymmetric conjugate addition of aryl boronic acid to 3-methyl cyclohexe-1-none to form quaternary carbon. Claisen rearrangement and subsequent aldol reaction furnished trans -decaline key intermediate, which assured a formal total synthesis of (−)-Triptophenolide and (+)-Triptolide. Graphical Abstract
ISSN:2192-2195
2192-2209
DOI:10.1007/s13659-016-0100-z