Journal ArticleDOI
An Efficient Two-Step Total Synthesis of the Quaterpyridine Nemertelline
Alexandre Bouillon,Anne Sophie Voisin,Audrey Robic,Jean-Charles Lancelot,Valérie Collot,Sylvain Rault +5 more
TLDR
Regioselective and univocal Suzuki cross-coupling reactions performed on halopyridinyl boronic acids provide a flexible and versatile route to a multigram scale synthesis of nemertelline, the quaterpyridine neurotoxin isolated from a Hoplonemertine sea worm.Abstract:
Regioselective and univocal Suzuki cross-coupling reactions performed on halopyridinyl boronic acids provide a flexible and versatile route to a multigram scale synthesis of 2,2'-dichloro-3,4'-bipyridine 14, which allows couplings with excess pyridin-3-yl boronic acid to give a new and efficient two-step rapid synthesis of nemertelline, the quaterpyridine neurotoxin isolated from a Hoplonemertine sea worm.read more
Citations
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Journal ArticleDOI
Chasing molecules that were never there: misassigned natural products and the role of chemical synthesis in modern structure elucidation.
TL;DR: It is made the case that imaginative detective work and chemical synthesis still have important roles to play in the process of solving nature's most intriguing molecular puzzles.
Journal ArticleDOI
Synthesis of Biaryls via Ligand‐Free Suzuki–Miyaura Cross‐Coupling Reactions: A Review of Homogeneous and Heterogeneous Catalytic Developments
TL;DR: The literature reporting ligand-free synthesis of biaryls from 2010 to May 2015 has been reviewed in this paper, and the catalysts outlined here allow convenient and green synthetic pathways specifically for the construction of C-C bonds.
Journal ArticleDOI
Highly selective metalations of pyridines and related heterocycles using new frustrated Lewis pairs or tmp-zinc and tmp-magnesium bases with BF3.OEt2.
TL;DR: In this article, the performance of the metalations using different hindered metal amide bases in the presence or absence of BF3·OEt2 was evaluated in terms of the functionalization of the heterocycles.
Journal ArticleDOI
Selective Palladium-Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes
TL;DR: This critical review with 341 references covers developments on the chemo- and site-selective Suzuki–Miyaura monocoupling reactions of polyhalogenated heteroarenes with different or identical halogen atoms.
Journal ArticleDOI
Iridium-catalyzed [2 + 2 + 2] cycloaddition of α,ω-diynes with nitriles.
Gen Onodera,Yoshihisa Shimizu,Jun-na Kimura,Junya Kobayashi,Yukiko Ebihara,Kei Kondo,Ken Sakata,Ryo Takeuchi +7 more
TL;DR: Regioselective cycloaddition of unsymmetrical diyne bearing two different internal alkyne moieties was achieved and could be reasonably explained by considering the different reactivities of the α-position in iridacyclopentadiene.
References
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Journal ArticleDOI
Functionalized Pyridylboronic Acids and Their Suzuki Cross-Coupling Reactions To Yield Novel Heteroarylpyridines
TL;DR: 6-chloro-2-methoxy-4-pyridylboronic acid 4 has been synthesized and shown to undergo palladium-catalyzed cross-coupling reactions with heteroaryl bromides to yield novel heteroarylpyridine derivatives.
Journal ArticleDOI
Solid-state structures of n-butyllithium-TMEDA, -THF, and -DME complexes
TL;DR: In this paper, solid-state structures for a series of n-butyllithium (n-BuLi)-N,N, N,N',N-,N'-tetramethylethylenediamine (TMEDA), N,B,THF, and DME complexes are presented.
Journal ArticleDOI
Radical Cyclization Routes to Bridged Pyranosides as Precursors of Densely Functionalized Cycloalkanes
TL;DR: Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group.
Journal ArticleDOI
A new convergent route to 1-substituted ellipticines
Journal ArticleDOI
Palladium-catalyzed cross-coupling of phenylboronic acid with heterocyclic aromatic halides
Johannes F. C. Stavenuiter,Martin Hamzink,Rob van der Hulst,Gijsbert Zomer,Gerard Westra,Erik Kriek +5 more
TL;DR: In this article, the reaction of l'acide phenylboronique avec des halogeno pyridines in presence of Pd(Ph 3 P) 4 : obtention de phenylpyridine.
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