Brønsted acid-catalyzed highly stereoselective arene-ynamide cyclizations. A novel keteniminium Pictet-Spengler cyclization in total syntheses of (+/-)-desbromoarborescidines A and C.
[reaction: see text] A Brønsted acid-catalyzed highly stereoselective arene-ynamide cyclization is described. These reactions constitute a keteniminium variant of Pictet-Spengler cyclizations, leading to efficient synthesis of nitrogen heterocycles and related alkaloids. Total syntheses of desbromoarborescidines A and C are illustrated here as first applications of this methodology.
Zhang
Yanshi
Y
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Hsung
Richard P
RP
Zhang
Xuejun
X
Huang
Jian
J
Slafer
Brian W
BW
Davis
Allison
A
D002384:Catalysis; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D026121:Indole Alkaloids; C506148:desbromoarborescidine A; C506149:desbromoarborescidine C