M. Breuning, M. Steiner
Aug 22, 2008
Citations
0
Influential Citations
11
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract The enantiomerically pure tricyclic 9-oxabispidine (1 R ,2 S ,9 S )-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.0 2,7 ]tridecane, a potential substitute for (+)-sparteine in asymmetric synthesis, was prepared in 7 steps and in 11% overall yield from a chiral epoxy alcohol and ( S )-epichlorohydrin. The key intermediate was a bicyclic 9-oxabispidine with an appropriately functionalized, endo -oriented side chain.