First total synthesis of a novel monoterpenoid isoquinoline alkaloid, (+/-)-alangine.
The structure including the stereochemistry of a novel monoterpenoid isoquinoline alkaloid, alangine, was confirmed by total synthesis via N-acyliminium cyclization to construct the isoquinoline skeleton and reductive cleavage of vinyl epoxide with Pd(0) catalyst.
Takayama
Hiromitsu
H
Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan. h.takayama@p.chiba-u.ac.jp
Arai
Maki
M
Kitajima
Mariko
M
Aimi
Norio
N
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D007546:Isoquinolines; D039821:Monoterpenes; C411301:alangine