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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Studies on Pumiliotoxin A Alkaloids: An Approach to Preparing the Indolizidinic Core by Intramolecular Diastereoselective N-Heterocyclic Carbene Catalyzed Benzoin Reaction

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Correia, Jose Tiago M. [1] ; Acconcia, Lais V. [1] ; Coelho, Fernando [1]
Total Authors: 3
[1] Univ Estadual Campinas, Inst Chem, POB 6154, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; n. 11, p. 1972-1976, APR 2016.
Web of Science Citations: 6

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 a(1) to d(1) - acyl anion equivalent) attacks a ketone moiety intramolecularly to provide the indolizidinone core in good yield with good selectivity. (AU)

FAPESP's process: 13/24386-5 - Syntheis and evaluation of the pharmacological potential of Pyrazolones and Pyrazolidinones, from Morita-Baylis-Hillman adducts
Grantee:Laís Vaz Acconcia
Support Opportunities: Scholarships in Brazil - Scientific Initiation
FAPESP's process: 13/10449-5 - Morita-Baylis-Hillman adducts as efficient building blocks for the synthesis of molecules of biological interest
Grantee:Fernando Antonio Santos Coelho
Support Opportunities: Regular Research Grants
FAPESP's process: 12/21809-0 - Organocatalysed synthesis of indolizidinic and quinolizidinic N-heterocycles from Morita-Baylis-Hillman adducts
Grantee:José Tiago Menezes Correia
Support Opportunities: Scholarships in Brazil - Doctorate
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC