1,2,9-三羥甲基-5,5-二甲基[4.4.0]雙環癸烷化合物之合成研究

Abstract

The purpose of this assignment is use different paths to synthesize 1,2,9-trihydroxymethyl-5,5-dimethyl bicyclo[4.4.0]decane. Through the fist path we got benzyloxydiene 29, however, there was only small product during the Diels-Alder reaction, therefore, in the second path we could not carry on successfully by with the Compound 40 in the ring closing reaction. Consequently, in path 3 and 4 we used 2-methylcyclohexanone 44 as the starting material to do the reaction and the result came out with vinylcyclohexen, and we got racemic mixture by using the DMAD in the Diels-Alder reaction. Further, we used the reduction again and we got racemic diol mixture. In path 3, we using different chriral reagent to do the chemical cutting but the result what we got was not separate. Therefore, so switch to path four of the conditions and found out that the racemic diol mixture 61 and（S）–（+）–ketopinic acid could do the reaction in the chemical cutting and we got Compound 63, Compound 64 as well as the dihydroxymethylbicyclo[4.4.0]decadiene 65. Moreover, by using the reduction with Compounds 63 we got dihydroxymethylbicyclo[4.4.0]decadiene 66. Last, we respectively the two enantiomer which were dihydroxymethyl bicyclo[4.4.0]decadiene 65 and dihydroxymethylbicyclo[4.4.0]decadiene 66 in the hydrogenation and deprotection were trihydroxymethylbicyclo[4.4.0]decane 68 and trihydroxymethyl bicyclo[4.4.0]decane 70.