Derivative Synthesis of Wanpeinine A,a Major Steroidal Alkaloid from Fritillaria shuchengensis

Objective To design and synthesize derivatives of wanpeinine A,the main steroidal alkaloid isolated from the plant Fritillaria shuchengensis,and further study on the structure-activity relationship of the steroidal alkaloid.Methods Acylation and alkylation were used to synthesize the derivatives and their structures were identified via NMR and MS.Results The acylation of wanpeinine A(1) produced 3β,6α-diacetylwanpeinine A(2),3β,6α-dipropionyl-wanpeinine A(3),3β,6α-dichloracetylwanpeinine A(4),3β,6α-dibenzoylwanpeinine A(5),and 3β-methoxy-acylwanpeinine A(6).The alkylation of wanpeinine A formed 3β,6α-dimethoxymethylwanpeinine A(7).Conclusion All compounds are new except for 3β,6α-diacetylwanpeinine A.