Organocatalytic enantioselective total synthesis of (-)-arboricine.
The tetracyclic indole alkaloid (-)-arboricine has been prepared using an asymmetric organocatalytic Pictet-Spengler reaction as the key step followed by a diastereoselective Pd-catalyzed iodoalkene/enolate cyclization. The absolute stereochemistry was unequivocally proven by X-ray crystallographic analysis and appeared to be opposite to the published structure in the original paper.
Wanner
Martin J
MJ
Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS, Amsterdam, The Netherlands.
Boots
Rowan N A
RN
Eradus
Bram
B
de Gelder
René
R
van Maarseveen
Jan H
JH
Hiemstra
Henk
H
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D026121:Indole Alkaloids; C544042:arboricine