Total synthesis of (±)-maistemonine and (±)-stemonamide.
The first total synthesis of polycyclic Stemona alkaloid maistemonine has been achieved. The efficient approach features a stereoselective intramolecular Schmidt reaction, a ketone-ester condensation, and a Reformatsky reaction. Additionally, another Stemona alkaloid stemonamide was divergently synthesized from a common intermediate.
State Key Laboratory of Applied Organic Chemistry & Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
Zhi-Hua
ZH
Chen
Yong-Qiang
YQ
Zhang
Zhi-Min
ZM
Chen
Yong-Qiang
YQ
Tu
Fu-Min
FM
Zhang
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D041901:Stemonaceae / Q000378:metabolism*; D013237:Stereoisomerism
D000470:Alkaloids; D004952:Esters; D007659:Ketones; D011083:Polycyclic Compounds; D013141:Spiro Compounds; C434309:stemonamide