Catalytic Asymmetric Total Synthesis of (+)-Yohimbine

• Published in: Organic letters Vol. 10; no. 5; pp. 745 - 748
• Main Authors: Mergott, Dustin J, Zuend, Stephan J, Jacobsen, Eric N
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.03.2008; Amer Chemical Soc
• Subjects: Catalysis; Chemistry; Chemistry, Organic; Cyclization; Molecular Structure; Physical Sciences; Science & Technology; Stereoisomerism; Yohimbine - chemical synthesis; Yohimbine - chemistry; ALCOHOLS; ESTER; YOHIMBINE; ORIGINS; CYCLIZATIONS; SERIES; DIELS-ALDER REACTIONS; STEREOSELECTIVITY; TRANSITION-STATES; INDOLE ALKALOIDS

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 intr...