Stereoselective synthesis of 7-epi-incarvilline.
The enantioselective synthesis of 7-epi-incarvilline for formal syntheses of (-)-incarvilline, (+)-incarvine C, and (-)-incarvillateine is described. The key features of our synthesis involve (1) stereoselective construction of the optically active bicyclic lactone utilizing Pd(0)-catalyzed allylic alkylation, (2) efficient transformation of the bridged bicyclic lactone to the key bicyclic lactam skeleton, and (3) stereoselective elaborations of two stereocenters via a substrate-controlled catalytic hydrogenation and a 1,4-addition.
College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Hyowon
H
Seo
Hwayoung
H
Yun
Sujin
S
Lee
Jaebong
J
Jang
Young Taek
YT
Han
Dae-Duk
DD
Kim
Jeeyeon
J
Lee
Young-Ger
YG
Suh
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D039821:Monoterpenes; C400141:incarvillateine