Tetrahedron

Synthesis of Polysubstituted Bicyclo [3.3. 1] nonane-3, 7-diones from Cyclohexa-2, 5-dienones and Dimethyl 1, 3-Acetonedicarboxylate

P Camps, A González, D Muñoz-Torrero, M Simon…

Index: Camps, Pelayo; Gonzalez, Albert; Munoz-Torrero, Diego; Simon, Montserrat; Zuniga, Adriana; Martins, Miriam A.; Font-Bardia, Merce; Solans, Xavier Tetrahedron, 2000 , vol. 56, # 41 p. 8141 - 8151

Full Text: HTML

Citation Number: 22

Abstract

Oxidation of polysubstituted phenols with phenyliodonium diacetate gives cyclohexa-2, 5- dienones, which on reaction with dimethyl 1, 3-acetonedicarboxylate afford double-Michael- addition derivatives, whose hydrolysis and decarboxylation provides polysubstituted bicyclo [3.3. 1] nonane-3, 7-diones. For steric and/or electronic reasons, the Michael reaction only works with 3, 5-unsubstituted or 3-substituted cyclohexa-2, 5-dienones, if the substituent is ...