Synthesis of the Leu - Trp Component of the Celogentin Family of Cyclic Peptides Through a C - H Activation - Cross-Coupling Strategy

2010 ◽  
Vol 63 (3) ◽  
pp. 438 ◽  
Author(s):  
Barbara T. Y. Li ◽  
Jonathan M. White ◽  
Craig A. Hutton
Keyword(s):  
Natural Products ◽  
Cyclic Peptides ◽  
Cyclic Peptide ◽  
Cross Coupling ◽  
Crystallographic Analysis ◽  
X Ray ◽  
Palladium Catalyzed ◽  
Coupling Strategy ◽  
The Cross ◽  
Single Stereoisomer

A bioinspired approach to the central leucine(C3)–tryptophan(C6) cross-linked moiety present in the celogentin family of cyclic peptide natural products was achieved. The key transformation was enabled through a palladium-catalyzed C–H activation–cross-coupling of leucine quinoline amide and 6-iodotryptophan derivatives. X-Ray crystallographic analysis of a β-(indol-6-yl)-leucine derivative confirms the stereochemistry of the cross-linked adduct matches that of the natural products. The method enables the preparation of the Leu–Trp adduct as a single stereoisomer from l-leucine and l-tryptophan.

Formal Total Syntheses of Crocacin A-D

2005 ◽  
Vol 70 (10) ◽  
pp. 1696-1708 ◽  
Author(s):  
Magnus Besev ◽  
Christof Brehm ◽  
Alois Fürstner
Keyword(s):  
Natural Products ◽  
Aldol Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
The Common ◽  
Selective Addition

A concise route to the common polyketide fragment5of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features asyn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzedanti-selective addition of propargyl mesylate10to the chiral aldehyde9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.

scholarly journals Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions

2010 ◽  
Vol 6 ◽  
Author(s):  
Tilman Lechel ◽  
Irene Brüdgam ◽  
Hans-Ulrich Reissig
Keyword(s):  
Crystal Structure ◽  
Crystal Packing ◽  
Cross Coupling ◽  
Crystal Structure Analysis ◽  
Coupling Reactions ◽  
X Ray ◽  
Cross Coupling Reactions ◽  
Fluorescence Measurements ◽  
Subsequent Conversion ◽  
Palladium Catalyzed

A series of trifluoromethyl-substituted 3-alkoxypyridinol derivatives has been deprotected to furnish pyridine-3,4-diol derivatives in good yields. The X-ray crystal structure analysis proved that a 1:1 mixture of pyridine-3,4-diols and their pyridin-4-one tautomers exist in the solid state. Subsequent conversion into bis(perfluoroalkanesulfonate)s were smoothly achieved. The obtained compounds were used as substrates for palladium-catalyzed coupling reactions. Fluorescence measurements of the biscoupled products showed a maximum of emission in the violet region of the spectrum.

Chemoselective reactions: Toward the synthesis of biologically active natural products with anticancer activities

2008 ◽  
Vol 80 (8) ◽  
pp. 1683-1691 ◽  
Author(s):  
Sébastien Reymond ◽  
Laurent Ferrié ◽  
Amandine Guérinot ◽  
Patrice Capdevielle ◽  
Janine Cossy
Keyword(s):  
Natural Products ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Biologically Active ◽  
Synthetic Approach ◽  
Anticancer Activities ◽  
Leucascandrolide A ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Active Natural

Leucascandrolide A and migrastatin were synthesized efficiently by using chemoselective reactions such as olefin metatheses. The use of an iron-catalyzed cross-coupling reaction overcame difficulties encountered with palladium-catalyzed processes in our synthetic approach toward spirangien A.

scholarly journals Ternatin and improved synthetic variants kill cancer cells by targeting the elongation factor-1A ternary complex

eLife ◽  
2015 ◽  
Vol 4 ◽  
Author(s):  
Jordan D Carelli ◽  
Steven G Sethofer ◽  
Geoffrey A Smith ◽  
Howard R Miller ◽  
Jillian L Simard ◽  
...  
Keyword(s):  
Natural Products ◽  
Cancer Cells ◽  
Cyclic Peptides ◽  
Ternary Complex ◽  
Cyclic Peptide ◽  
Hot Spot ◽  
Elongation Factor ◽  
Hydrophobic Surface ◽  
Eukaryotic Elongation Factor ◽  
Domain Iii

Cyclic peptide natural products have evolved to exploit diverse protein targets, many of which control essential cellular processes. Inspired by a series of cyclic peptides with partially elucidated structures, we designed synthetic variants of ternatin, a cytotoxic and anti-adipogenic natural product whose molecular mode of action was unknown. The new ternatin variants are cytotoxic toward cancer cells, with up to 500-fold greater potency than ternatin itself. Using a ternatin photo-affinity probe, we identify the translation elongation factor-1A ternary complex (eEF1A·GTP·aminoacyl-tRNA) as a specific target and demonstrate competitive binding by the unrelated natural products, didemnin and cytotrienin. Mutations in domain III of eEF1A prevent ternatin binding and confer resistance to its cytotoxic effects, implicating the adjacent hydrophobic surface as a functional hot spot for eEF1A modulation. We conclude that the eukaryotic elongation factor-1A and its ternary complex with GTP and aminoacyl-tRNA are common targets for the evolution of cytotoxic natural products.

A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A

2017 ◽  
Vol 82 (8) ◽  
pp. 4148-4159 ◽  
Author(s):  
Qiao Yan ◽  
Emma Gin ◽  
Malgorzata Wasinska-Kalwa ◽  
Martin G. Banwell ◽  
Paul D. Carr
Keyword(s):  
Natural Products ◽  
Cross Coupling ◽  
Reductive Cyclization ◽  
Palladium Catalyzed

Palladium-Catalyzed Thiomethylation via a Three-Component Cross-Coupling Strategy

2018 ◽  
Vol 20 (19) ◽  
pp. 6193-6197 ◽  
Author(s):  
Ming Wang ◽  
Zongjun Qiao ◽  
Jiaoyan Zhao ◽  
Xuefeng Jiang
Keyword(s):  
Cross Coupling ◽  
Palladium Catalyzed ◽  
Coupling Strategy

Synthesis of Natural Products via Palladium-Catalyzed Cross-Coupling

ChemInform ◽  
2003 ◽  
Vol 34 (25) ◽  
Author(s):  
Ze Tan ◽  
Ei-ichi Negishi
Keyword(s):  
Natural Products ◽  
Cross Coupling ◽  
Palladium Catalyzed

Synthesis of 24-phenyl-24-oxo steroids derived from bile acids by palladium-catalyzed cross coupling with phenylboronic acid. NMR characterization and X-ray structures

Steroids ◽  
2013 ◽  
Vol 78 (11) ◽  
pp. 1092-1097 ◽  
Author(s):  
Martha C. Mayorquín-Torres ◽  
Margarita Romero-Ávila ◽  
Marcos Flores-Álamo ◽  
Martin A. Iglesias-Arteaga
Keyword(s):  
Bile Acids ◽  
Phenylboronic Acid ◽  
Cross Coupling ◽  
X Ray ◽  
Nmr Characterization ◽  
Palladium Catalyzed
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