Catalytic asymmetric total synthesis of (+)-yohimbine.
The total synthesis of (+)-yohimbine was achieved in 11 steps and 14% overall yield. The absolute configuration was established through a highly enantioselective thiourea-catalyzed acyl-Pictet-Spengler reaction, and the remaining 4 stereocenters were set simultaneously in a substrate-controlled intramolecular Diels-Alder reaction.
Mergott
Dustin J
DJ
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Zuend
Stephan J
SJ
Jacobsen
Eric N
EN
D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism; D015016:Yohimbine / Q000138:chemical synthesis* / Q000737:chemistry
D015016:Yohimbine