Concise synthesis of 22-hydroxyacuminatine, cytotoxic camptothecinoid from Camptotheca acuminata, by pyridone benzannulation.
A short, efficient synthesis of 22-hydroxyacuminatine, starting from a readily accessible hydroxy pyridone, is presented; key steps include a Heck coupling with methyl pentadienoate, a flash vacuum pyrolytic cyclization, and a Friedländer condensation.
Babjak
Matej
M
Université Joseph Fourier de Grenoble, Chimie Recherche (LEDSS), 38041, Grenoble, France.
Kanazawa
Alice
A
Anderson
Regan J
RJ
Greene
Andrew E
AE
D029769:Camptotheca / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*
C508964:22-hydroxyacuminatine; D007212:Indolizines; D011728:Pyridones; D011804:Quinolines