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

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.

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.

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

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.

scholarly journals Catalyst Controlled Regiodivergent C-H Alkynylation of Thiophenes

2020 ◽  
Author(s):  
Arup Mondal ◽  
Manuel van Gemmeren
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Bioactive Molecules ◽  
Reaction Conditions ◽  
Common Procedure ◽  
Broad Scope ◽  
Palladium Catalyzed

Alkynes are highly attractive motifs in organic synthesis due to their presence in natural products and bioactive molecules as well as their versatility in a plethora of subsequent transformations. A common procedure to insert alkynes into hetero(arenes), such as the thiophenes studied herein, consists of a halogenation followed by a Sonogashira cross-coupling. The regioselectivity of this approach depends entirely on the halogenation step. Similarly, direct alkynylations of thiophenes have been described that follow the same regioselectivity patterns. Herein we report the development of a palladium catalyzed C–H activation/alkynylation of thiophenes. The method is applicable to a broad range of thiophene substrates. For 3-substituted substrates where controlling the regioselectivity between the C2 and C5 position is particularly challenging, two sets of reaction conditions enable a regiodivergent reaction, giving access to each regioisomer selectively. Both protocols use the thiophene as limiting reagent and show a broad scope, rendering our method suitable for late-stage modification.

scholarly journals Catalyst Controlled Regiodivergent C-H Alkynylation of Thiophenes

2020 ◽  
Author(s):  
Arup Mondal ◽  
Manuel van Gemmeren
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Bioactive Molecules ◽  
Reaction Conditions ◽  
Common Procedure ◽  
Broad Scope ◽  
Palladium Catalyzed

Alkynes are highly attractive motifs in organic synthesis due to their presence in natural products and bioactive molecules as well as their versatility in a plethora of subsequent transformations. A common procedure to insert alkynes into hetero(arenes), such as the thiophenes studied herein, consists of a halogenation followed by a Sonogashira cross-coupling. The regioselectivity of this approach depends entirely on the halogenation step. Similarly, direct alkynylations of thiophenes have been described that follow the same regioselectivity patterns. Herein we report the development of a palladium catalyzed C–H activation/alkynylation of thiophenes. The method is applicable to a broad range of thiophene substrates. For 3-substituted substrates where controlling the regioselectivity between the C2 and C5 position is particularly challenging, two sets of reaction conditions enable a regiodivergent reaction, giving access to each regioisomer selectively. Both protocols use the thiophene as limiting reagent and show a broad scope, rendering our method suitable for late-stage modification.

Palladium-Catalyzed Cross Coupling Reactions of β-Iodo-β,γ-enones with Organozinc Chlorides

1997 ◽  
Vol 62 (6) ◽  
pp. 1908-1908
Author(s):  
Fen-Tair Luo ◽  
Li-Chen Hsieh
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Suzuki–Miyaura cross-coupling for chemoproteomic applications

2020 ◽  
Author(s):  
Jian Cao ◽  
Ernest Armenta ◽  
Lisa Boatner ◽  
Heta Desai ◽  
Neil Chan ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Cross Coupling ◽  
Protein Profiling ◽  
Protein Labeling ◽  
Caspase 8 ◽  
Complex Cell ◽  
Bioorthogonal Chemistry ◽  
Reaction Conditions ◽  
Target Deconvolution ◽  
Palladium Catalyzed

Bioorthogonal chemistry is a mainstay of chemoproteomic sample preparation workflows. While numerous transformations are now available, chemoproteomic studies still rely overwhelmingly on copper-catalyzed azide –alkyne cycloaddition (CuAAC) or 'click' chemistry. Here we demonstrate that gel-based activity-based protein profiling (ABPP) and mass-spectrometry-based chemoproteomic profiling can be conducted using Suzuki–Miyaura cross-coupling. We identify reaction conditions that proceed in complex cell lysates and find that Suzuki –Miyaura cross-coupling and CuAAC yield comparable chemoproteomic coverage. Importantly, Suzuki–Miyaura is also compatible with chemoproteomic target deconvolution, as demonstrated using structurally matched probes tailored to react with the cysteine protease caspase-8. Uniquely enabled by the observed orthogonality of palladium-catalyzed cross-coupling and CuAAC, we combine both reactions to achieve dual protein labeling.

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