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

Author(s)

Correia, Jose Tiago M. ; Acconcia, Lais V. ; Coelho, Fernando

• Document type: Journal article
• Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2016, n. 11, p. 5-pg., 2016-04-01.

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 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: 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: 13/24386-5 - 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: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• 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