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An Efficient Approach to the Securinega Alkaloids Empowered by Cooperative N‐Heterocyclic Carbene/Lewis Acid Catalysis
Author(s) -
ElSohly Adel M.,
Wespe Daniel A.,
Poore Tyler J.,
Snyder Scott A.
Publication year - 2013
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.201301849
Subject(s) - intramolecular force , carbene , chemistry , computer science , lewis acids and bases , domain (mathematical analysis) , butenolide , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , mathematics , mathematical analysis
Folding it all together : Most of the syntheses developed for the securinega alkaloid class require lengthy sequences to create their bridging butenolide domains. A novel approach uses N‐heterocyclic carbenes (NHCs) and Lewis acids to forge the entire domain in a single step from appropriate precursors, showing that ynal‐derived homoenolates can participate as nucleophiles in intramolecular settings (see scheme).