Organocatalytic
Enantioselective Total Synthesis of (-)-Arboricine
Wanner MJ , Boots RNA, Eradus B, de Gelder R , van Maarseveen JH ,
Hiemstra H
ORGANIC LETTERS Volume: 11 Issue:
12 Pages: 2579-2581 Published: JUN
18 2009
Abstract:
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.