Synthesis and functionalization of nitrogen heterocycle catalyzed by metal transition. Toward the total synthesis of (-)-norsuaveoline.
type: Dataset
description: These scientific project deals with synthesis and functionalization of nitrogen heterocycles catalyzed by transition metals. The first part of this project was devoted to the development of a simple and efficient reaction for the N-cyclopropylation of various nitrogen compounds. From cyclopropylboronic acid under copper oxidative coupling conditions, a wide variety of nitrogen compounds have been N-cyclopropylated. This method allows a new access to N-cyclopropylated substrates.The second part of this work deals with benzimidazoles synthesis. These nitrogen heterocycles have been obtained from amidines through a sequence involving a N-arylation reaction followed by cyclization via a C-H bond functionalization.The third part of this manuscript focuses on pyrroles synthesis. Pyrroles are known for their abundance in biologically active molecules. We have developed a new sequential one-pot procedure for poly-functionalized N-H pyrroles synthesis. Through a enaminone formation catalyzed by indium (III), followed by a palladium catalyzed heteroannulation, various N-H pyrroles have been synthesizedThe final part of this scientific project describes our approach to total synthesis of an alkaloid: the (-)-norsuavéoline. The specificity of our approach was based on the formation of pyridine ring in the beginning of the synthesis and a late formation of indole ring. To date, we have developed and optimized the pyridine synthesis from L-(-)-glutamic acid. Studies are ongoing in the laboratory to obtain the indole part and complete the synthesis of this natural product.
identifier: NNT: 2011PA112310
issued: 2026-05-08T00:20:57.339490
language: fr
modified: 2026-05-08T00:20:57.339494
contact point: Organization
  fn: CCSD
keyword: --norsuaveoline
keyword: alcaloide
keyword: alkaloid
keyword: benzimidazoles
keyword: catalyse
keyword: catalysis
keyword: chimothechemical-sciencesother
keyword: copper
keyword: couplage-en-conditions-oxydantes
keyword: cuivre
keyword: heteroannelation
keyword: heteroannulation
keyword: heterocycles-azotes
keyword: infoeu-reposemanticsdoctoralthesis
keyword: n-cyclopropylation
keyword: nitrogen-heterocycles
keyword: oxidative-cross-coupling
keyword: palladium
keyword: pyrroles
keyword: theses
landing page: https://theses.hal.science/tel-00912326

Synthesis and functionalization of nitrogen heterocycle catalyzed by metal transition. Toward the total synthesis of (-)-norsuaveoline.
type: Distribution
format: HTML
issued: 2026-05-08T00:20:57.344537
modified: 2026-05-08T00:20:57.321517
access URL: https://theses.hal.science/tel-00912326

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type: Agent