Synthesis of cedranoid sesquiterpenes. II. Functionalization at carbon 12
P Yates, KE Stevens
Index: Yates, Peter; Stevens, Kenneth E. Canadian Journal of Chemistry, 1982 , vol. 60, p. 825 - 834
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Citation Number: 17
Abstract
Dimethyl 6, 6-dimethyl-7-oxotricyclo [3.2. 1.02, 8] octane-1, 8-dicarboxylate (6) undergoes homoconjugate addition with lithium diphenylcuprate to give dimethyl 3-hydroxy-4, 4- dimethyl-exo-8-phenyl-cis-bicyclo [3.3. 0] oct-2-ene-1, 2-dicarboxylate (12 a), which on monodecarboxymethylation, ozonolysis, and esterification with diazomethane gives dimethyl 6, 6-dimethyl-7-oxo-cis-bicyclo-[3.3. 0] octane-1, exo-2-dicarboxylate (15). ...
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[Holm, Torkil Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1981 , p. 464 - 467]