Add time:08/18/2019         Source:sciencedirect.com

The reactions of 3,6-dibromo-2,7-dioxotetracyclo[6.3.0.04,11.05,9]undecane with organomagnesium halides are investigated as a method of preparing unusual tetrasubstituted pentacycloundecanes (D3-trishomocubanes). The tetrasubstituted pentacycloundecanes have been characterized and product geometries confirmed by NMR and X-ray crystal structure analysis. Rel-(1R,2R,3S,4S,5R,6R,7S,8S,9R,10R)-4-hydroxy-4-phenyl-6-methyl-7-bromo-(D3)-trishomocubane (11) exhibits a sterically locked phenyl group with a rotation barrier > 17 kcal/mol which should make possible the preparation of stable rotational isomers with o- or m-substituted phenyl groups.

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