The o-xylylene protecting group as an element of conformational control of remote stereochemistry in the synthesis of spiroketals.
Protection of trans-1,2-diol segments as cyclic o-xylylene ethers strongly favours diequatorial over diaxial dispositions; the possibility of using this grouping for remote control of the stereochemistry in the synthesis of spiroketals is here demonstrated by the stereoselective synthesis of tricyclic spirodisaccharides (di-D-fructose dianhydrides).
Balbuena
Patricia
P
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado 553, E-41071, Sevilla, Spain.
Rubio
Enrique M
EM
Ortiz Mellet
Carmen
C
García Fernández
José M
JM