Abstract
This thesis is divided into three parts. The first part describes the synthesis of antiemetic drug – Aloxi analogs. The second and third parts describe the application of camphor derived chiral ligand in catalytic asymmetric carbon-carbon bond formation reaction. 1.Antiemetic drug synthesis : Aloxi is a potent antiemetic drugs for the treatment of CINV (chemotherapy-induced nausea and vomiting). We synthesize some Aloxi analogs from Benz[cd]indol-2(1H)-one 1 and α-Tetralone 20. The medical activity of these analogs could be simply evaluated by radio ligand binding assay. By comparing the activity with Aloxi, we can probe the difference results from the structure and substitution. The inhibition of 5-HT serotonin could be up to 99% by compound 27 in 10 μM. 2.Asymmetric cyanohydrin synthesis : To improve the complex aggregation during the preparation of Titanium complex, we utilize Ti(OtBu)4 as Titanium source. In the presence of 5.5 mol% chiral ligand 30 and 5 mol% Ti(OtBu)4, the complex generated in situ could serve as a good catalyst for the cyanosilylation of aldehyde. Under optimized condition, the cyanohydrin could be obtained in up to 96% yield and 99%ee. 3.Asymmetric addition of alkenylzinc to aldehydes : The application of (-)-SMOTIB in asymmetric addition of alkenylzinc to aldehydes, and the corresponding (E)-allylic alcohols could be obtained in up to > 99% ee as well as good yield.