An Efficient Approach to the Securinega Alkaloids Empowered by Cooperative N‐Heterocyclic Carbene/Lewis Acid Catalysis1. Issue 22 (22nd April 2013)

• Record Type: Journal Article
• Authors: ElSohly, Adel M.; Wespe, Daniel A.; Poore, Tyler J.; Snyder, Scott A.
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 22(2013)
• Page Start: 5789
• Page End: 5794
• Publication Date: 2013-04-22
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201301849
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Folding it all together</bold>: 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).<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg20p497k3" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>