P. Camps, A. E. Lukach, S. Vázquez
Mar 17, 2001
Citations
0
Influential Citations
6
Citations
Journal
Tetrahedron
Abstract
Abstract The strain of the bisnoradamantane skeleton is shown by: (i) the easy homoketonization of tricyclo[3.3.0.0 3,7 ]octane-1,5-diol, 2a , to exo -7-hydroxy- cis -bicyclo[3.3.0]octan-3-one, 3a , under silica gel column chromatography, and (ii) the cleavage of the C3–C7 bond of 1,5-dimethyl-3,7-dipivaloyltricyclo[3.3.0.0 3,7 ]octane, 9 , to give bicyclo[3.3.0]octane diketones, under attempted SmI 2 -intramolecular pinacolization. In contrast, 2a was obtained by SmI 2 -pinacolization of cis-bicyclo[3.3.0]octane-3,7-dione, 1a .