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A Novel Approach to the Pyridoacridine Ring System: Synthesis of the Topoisomerase Inhibitor 13‐Deazaascididemin
Author(s) -
Raeder Stephan,
Bracher Franz
Publication year - 2012
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201200019
Subject(s) - regioselectivity , ring (chemistry) , chemistry , annulation , stereochemistry , alkaloid , topoisomerase , radical cyclization , homolysis , combinatorial chemistry , radical , organic chemistry , enzyme , catalysis
A novel approach to the pyridoacridine ring system of the ascididemin‐type marine alkaloids is presented. This approach allows for the introduction of the ring A of the alkaloids by using a simple aromatic aldehyde building block. The viability of this approach is demonstrated with the synthesis of AK37, a bioactive deaza analogue of the alkaloid ascididemin. Starting from 3‐cyano‐4‐methylquinoline, a sequence of regioselective homolytic benzoylation, annulation of a bromopyridine ring, and radical cyclization leads to the pentacyclic ring system.