Oxazatricyclic noradamantanes: stereocontrolled synthesis of functionalized scopolines, related cage molecules, and drug leads.
Scopolines 4 and the noradamantane scaffold are accessible from 8-oxabicyclo[3.2.1]oct-6-en-3-ones such as 6 by a concise route involving introduction of an axial amino nitrogen at C3, epoxidation, and cyclization. The resulting cage molecules are versatile drug leads.
Pascual
María Vidal
MV
Department of Organic Chemistry, University of Hannover, D-30167 Hannover.
Proemmel
Steffen
S
Beil
Winfried
W
Wartchow
Rudolf
R
Hoffmann
H M R
HM
D000218:Adamantane / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis*
D000470:Alkaloids; D000218:Adamantane