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.

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2006-02, Vol.4 (3), p.407-409
Main Authors: Babjak, Matej, Kanazawa, Alice, Anderson, Regan J, Greene, Andrew E
Format: Article
Language:English
Subjects:
Camptotheca - chemistry
Indolizines - chemical synthesis
Indolizines - chemistry
Indolizines - toxicity
Molecular Structure
Pyridones - chemistry
Quinolines - chemical synthesis
Quinolines - chemistry
Quinolines - toxicity
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Description
Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b516154a