Highly Stereoselective Synthesis Of The Intermediate For Demethoxyfumitremorgin C And Microwave-Assisted Synthesis Of Azaindole

This thesis has studied the stereoselectivity of the synthesis of anti-cancer drug demethoxyfumitremorgin C. In addition, we have found a microwave-assisted method for synthesis of azaindoles. The two parts are described below:(1) Many synthetic routes to demethoxyfumitremorgin C have been reported, but the yield of each route is not high enough, due to the low stereoselectivity of the formation of basic skeleton-cis-1,3-disubstituted-1,2,3,4-tetrahydro-β-carboline.We have found a highly stereoselective approach to the cis-1,3-disubstituted-1,2,3,4-tetrahydro-β-carboline, and then applied it to the synthesis of demethoxy fumitremorgin C. Herein, we synthesized the3,4-dihydro-β-carboline via Bischler-Napieralski reaction, followed by reduction with NaBH4to afford the cis-1,3-disubstituted-1,2,3,4-tetrahydro-β-carboline. We applied this route to generate the tetrahydro-β-carboline skeleton of demethoxyfumitremorgin C, and the reaction has showed high stereoselectivity.(2) When we synthesized the azaindole Ⅱ-2g, a microwave-assisted method have been found. When pyridine hydrazines were treated with Ph-Ph/Ph-O-Ph mixture under microwave, they went through a Fisher indole reaction, to afford various azaindole derivatives. Using this method, we can get the4-,5-,6-and7-azaindole quickly and concisely under a catalyst-free condition. In the synthesis of specific azaindoles, the reaction showed an interesting regioselectivity.