An efficient Au-catalyzed synthesis of isomukonidine, clausine L, mukonidine, glycosinine, mukonal, and clausine V from propadienyl methyl ether.
Naturally occurring carbazole alkaloids such as isomukonidine, clausine L, mukonidine, glycosinine, mukonal, and clausine V have been synthesized through a gold-catalyzed cyclization reaction of 1-(indol-2-yl)-2-methoxy-2,3-allenols, which are readily available from indolecarbaldehydes and methoxypropadiene. Compared to the reported procedures, our approach is general, atom economic, highly selective, and the starting materials are easily available.
Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China.
Youai
Y
Qiu
Dengke
D
Ma
Chunling
C
Fu
Shengming
S
Ma
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D008738:Methyl Ethers / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D002227:Carbazoles; D008738:Methyl Ethers; C531182:clausine L; D006046:Gold