T. Chou, Jong‐Hsin Chiou
Sep 1, 1986
Citations
0
Influential Citations
15
Citations
Journal
Journal of The Chinese Chemical Society
Abstract
The title compound (7) was synthesized in six steps from 1,8,9,10-tetrachloro-11,11-dimethoxy-endo-tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione (4) in an overall yield of 36%. The key intermediate, 1,8,9,10-tetrachloro-11,11-dimethoxy-endo-tricyclo-[6.2.1.02,7]undeca-3,5,9-triene (12), obtained from 4 by reduction, mesylation and then 1,4-elimination, was allowed to react with diethyl azodicarboxylate to afford the Diels-Alder adduct 16. Photochemical closure of 16, followed by hydrolysis and decarboxylation, gave the title compound. The title compound failed to give either the homopentaprismanone derivative 3 or the diene 9 by the photochemical or thermal elimination of molecular nitrogen.