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- Title
Studies on Pumiliotoxin A Alkaloids: An Approach to Preparing the Indolizidinic Core by Intramolecular Diastereoselective N-Heterocyclic Carbene Catalyzed Benzoin Reaction.
- Authors
Correia, José Tiago M.; Acconcia, Laís V.; Coelho, Fernando
- Abstract
In this article, we describe the development of a convergent organocatalytic strategy to prepare the indolizidinic core of the pumiliotoxin A alkaloid family. The key step of the proposed strategy is based on a diastereoselective N-heterocyclic carbene catalyzed benzoin reaction, in which the Breslow intermediate generated from an enal moiety (umpolung a1 to d1 - acyl anion equivalent) attacks a ketone moiety intramolecularly to provide the indolizidinone core in good yield with good selectivity.
- Subjects
PUMILIOTOXINS; INDOLIZIDINES synthesis; STEREOSELECTIVE reactions; BENZOIN; CARBENE synthesis; ORGANOCATALYSIS; UMPOLUNG; ASYMMETRIC synthesis
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 11, p1972
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600172