Synthesis of cedranoid sesquiterpenes. III. Functionalization at carbon 4

P Yates, DJ Burnell, VJ Freer…

Index: Yates, Peter; Burnell, D. Jean; Freer, Vernon J.; Sawyer, Jeffery F. Canadian Journal of Chemistry, 1987 , vol. 65, p. 69 - 77

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Citation Number: 21

Abstract

Dimethyl 6, 6-dimethyl-5, 7-dioxobicyclo [2.2. 2] oct-2-ene-2, 3-dicarboxylate (8) on irradiation in acetophenone gives dimethyl 6, 6-dimethyl-4, 7-dioxotricyclo [3.2. 1.02, 8] octane-1, 8-dicarboxylate (13), which on treatment with lithium dimethylcuprate followed by monodecarbomethoxylation gives methyl 4, 4-endo-8-trimethyl-3, 6-dioxo-cis-bicyclo [3.3. 0] octane-1-carboxylate (17). Similar irradiation of dimethyl 4, 6, 6-trimethyl-5, 7-dioxobicyclo ...