Synthesis of pyrroloindolines and furoindolines via cascade dearomatization of indole derivatives with carbenium ion.
A highly efficient intermolecular cascade dearomatization of substituted indoles with benzodithiolylium tetrafluoroborate has been developed. This reaction provides a novel strategy to synthesise C3 methyl-substituted pyrroloindolines and furoindolines under mild reaction conditions, the utility of which has been demonstrated by the synthesis of esermethol and physovenine in a highly concise manner.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China. slyou@sioc.ac.cn.
Chuan
C
Liu
Qin
Q
Yin
Li-Xin
LX
Dai
Shu-Li
SL
You
D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D010830:Physostigmine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001881:Borates; D005663:Furans; D007211:Indoles; D011758:Pyrroles; C518152:esermethole; C092643:physovenine; D010830:Physostigmine