General approach to the synthesis of polyquinenes. VIII. Synthesis of triquinacene, 1, 10-dimethyltriquinacene, and 1, 10-cyclohexanotriquinacene

…, GS Lannoye, G Kubiak, J Schkeryantz…

Index: Gupta, Ashok K.; Lannoye, Greg S.; Kubiak, Greg; Schkeryantz, Jeff; Wehrli, Suzanne; Cook, James M. Journal of the American Chemical Society, 1989 , vol. 111, # 6 p. 2169 - 2179

Full Text: HTML

Citation Number: 22

Abstract

Abstract: The synthesis of tricycl0 [5.2. 1.0~*~~] deca-2, 5, 8-triene (I), I, lO-dimethyltricyclo [5.2. 1. 04, 10] deca-2, 5, 8-triene (3), and tetracycl0 [5.5. 2.0~~*. O~*~] tetradeca-2, 5, 13- triene (4) has been accomplished via the reaction of 1, 2-dicarbonyl compounds with di-tert- butyl 3-oxoglutarate (Weiss reaction). Condensation of glyoxal Sa with di-tert-butyl 3- oxoglutarate (6b) gave the tetra-tert-butyl cis-dioxobicyclo [3.3. O] octane-2, 4, 6, 8- ...