THE SYNTHESIS AND BASE INDUCED HOMOKETONIZATION OF 5-SUBSTITUTED HOMOCUNEYL 4-ACETATES

Article abstract of DOI:10.1016/S0040-4020(01)82454-6

The synthesis of two 5-substituted homocuneyl 4-acetates viz 4-acetoxy-5-carbomethoxypentacyclo<4.3.0.0^2.4.0^3.8.0^5.7>nonane (8) and 4-acetoxy-5-benzoylpentacyclo<4.3.0.0^2.4.0^3.8.0^5.7>nonane (9) is described starting from dicarboxylic acid (10).The base induced cage opening of these acetates has been studied.It was found for 9 that the regiochemistry of this process is not affected by the carbonyl containing functionality at C₅.Exclusive opening of the cyclopropanol ring is observed.