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Highly Efficient Synthesis of Tricyclic Amines by a Cyclization/Cycloaddition Cascade: Total Syntheses of Aspidospermine, Aspidospermidine, and Quebrachamine
Author(s) -
Coldham Iain,
Burrell Adam J. M.,
White Laura E.,
Adams Harry,
Oram Niall
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200701943
Subject(s) - cycloaddition , intramolecular force , alkene , chemistry , tandem , cascade , stereochemistry , amine gas treating , combinatorial chemistry , organic chemistry , catalysis , materials science , chromatography , composite material
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).