Highly Selective Entry to the Azadirachtin Skeleton via a Claisen Rearrangement/Radical Cyclization Sequence

Highly Selective Entry to the Azadirachtin Skeleton via a Claisen Rearrangement/Radical Cyclization Sequence

A highly diastereoselective, microwave-induced Claisen rearrangement of an appropriately substituted propargylic enol ether allows the formation of the sterically congested C8−C14 bond of azadirachtin. When combined with a radical-mediated cyclization of the corresponding allene, this sequence offer...

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Veröffentlicht in:Organic letters 2002-10, Vol.4 (22), p.3847-3850
Hauptverfasser: Durand-Reville, Thomas, Gobbi, Luca B, Gray, Brian Lawrence, Ley, Steven V, Scott, James S
Format: Artikel
Sprache:eng
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Zusammenfassung:A highly diastereoselective, microwave-induced Claisen rearrangement of an appropriately substituted propargylic enol ether allows the formation of the sterically congested C8−C14 bond of azadirachtin. When combined with a radical-mediated cyclization of the corresponding allene, this sequence offers rapid entry to the framework of azadirachtin.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0201557