Radical Cyclization of N-Acylcyanamides: Total Synthesis of Luotonin A

As radical chain cascade precursors, N‐acylcyanamides give rise to amide–iminyl radicals which, when appropriately substituted, can finally yield pyrroloquinazolines. The versatility of these new radical acceptors is illustrated by the formation of N‐heterocycles with wide structural variation and b...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2007-01, Vol.46 (4), p.576-579
Main Authors: Servais, Aurore, Azzouz, Mériam, Lopes, David, Courillon, Christine, Malacria, Max
Format: Article
Language:English
Subjects:
alkaloids
Cyanamide - chemistry
cyanamides
Cyclization
nitrogen heterocycles
Pyrroles - chemical synthesis
Quinones - chemical synthesis
radicals
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Summary:As radical chain cascade precursors, N‐acylcyanamides give rise to amide–iminyl radicals which, when appropriately substituted, can finally yield pyrroloquinazolines. The versatility of these new radical acceptors is illustrated by the formation of N‐heterocycles with wide structural variation and by the total synthesis of luotonin A.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200602940