Highly Efficient Synthesis of Tricyclic Amines by a Cyclization/Cycloaddition Cascade: Total Syntheses of Aspidospermine, Aspidospermidine, and Quebrachamine

Three in one: Three new rings can be made in one pot with complete control of the regio‐ and stereochemistry by a tandem cyclization/cycloaddition cascade reaction. Treatment of a chloroaldehyde with an amine gives a cyclic azomethine ylide that undergoes intramolecular cycloaddition onto a tethered...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2007-01, Vol.46 (32), p.6159-6162
Main Authors: Coldham, Iain, Burrell, Adam J.M, White, Laura E, Adams, Harry, Oram, Niall
Format: Article
Language:English
Subjects:
alkaloids
amines
Cyclization
cycloaddition
Indole Alkaloids - chemical synthesis
Quinolines - chemical synthesis
ylides
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Summary:Three in one: Three new rings can be made in one pot with complete control of the regio‐ and stereochemistry by a tandem cyclization/cycloaddition cascade reaction. Treatment of a chloroaldehyde with an amine gives a cyclic azomethine ylide that undergoes intramolecular cycloaddition onto a tethered alkene. The method was applied to the shortest known synthesis of aspidospermine (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200701943