119595-41-4Relevant academic research and scientific papers
6-Substituted Bicyclohept-5-en-2-one Ketals
Lal, Kasturi,Salomon, Robert G.
, p. 2628 - 2632 (1989)
Structurally specific syntheses of isomerically pure 6-substituted bicyclohept-5-en-2-one ketals were explored.A conversion of the Diels-Alder adduct of itaconic anhydride with cyclopenta-1,3-diene into a ketal of 6-methylbicyclohept-5-en-2-one was accomplished, but the last step, an oxidative vicinal bisdecarboxylation, gave only a 35percent yield.The ethylene ketal of 6-methylbicyclohept-5-en-2-one was prepared in 80percent overall yield from bicyclohept-5-en-2-one by a regioselective replacement of hydrogen with a methyl group.Practical synthesesof the 6-bromo, 6-carbomethoxy, 6-phenylthio, and 6-trimethylsilyl analogues were accomplished similarly.
