Total synthesis of pareitropone via radical anion coupling.
A concise (9-step) synthesis of the tropoloisoquinoline alkaloid pareitropone has been achieved starting from 2-bromoisovanillin. The key step features oxidative cyclization of a readily available phenolic nitronate for the convenient construction of the fused tropone ring. This work underscores the synthetic utility of intramolecular oxidative coupling reactions of phenolic nitronates.
Hong
Suk-Koo
SK
Department of Chemical and Biological Engineering, Seoul National University, Seoul, 151-744, Republic of Korea.
Kim
Hyeonjeong
H
Seo
Youngran
Y
Lee
Sang Hyup
SH
Cha
Jin Kun
JK
Kim
Young Gyu
YG
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000838:Anions; D001547:Benzaldehydes / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
C553778:2-bromoisovanillin; D000470:Alkaloids; D000838:Anions; D001547:Benzaldehydes; D006842:Hydrocarbons, Brominated; D007546:Isoquinolines; C467752:pareitropone