scholarly journals Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers

2019 ◽  
Vol 10 (11) ◽  
pp. 3223-3230 ◽  
Author(s):  
Paola Caramenti ◽  
Nina Declas ◽  
Romain Tessier ◽  
Matthew D. Wodrich ◽  
Jerome Waser
Keyword(s):  
Natural Products ◽  
Room Temperature ◽  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Alkyl Aryl ◽  
Enol Ethers ◽  
Coupling Strategy

Highly stereoselective synthesis of Z-enamides and enol ethers at room temperature via an umpolung/cross coupling strategy applicable to drugs and natural products.

ChemInform Abstract: Hydrostannylation-Cross-Coupling Strategy for the Stereoselective Synthesis of Alkylidenemalonates and Related α,β-Unsaturated Esters.

ChemInform ◽  
2015 ◽  
Vol 46 (25) ◽  
pp. no-no
Author(s):  
Shinichi Fujiwara ◽  
Romain Cadou ◽  
Yousuke Yamaoka ◽  
Kiyosei Takasu ◽  
Ken-ichi Yamada
Keyword(s):  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Unsaturated Esters ◽  
Coupling Strategy

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.

A [bmim]Cl-promoted domino protocol using an isocyanide-based [4+1]-cycloaddition reaction for the synthesis of diversely functionalized 3-alkylamino-2-alkyl/aryl/hetero-aryl indolizine-1-carbonitriles under solvent-free conditions

2020 ◽  
Vol 44 (8) ◽  
pp. 3241-3248 ◽  
Author(s):  
Amol Balu Atar ◽  
Jongmin Kang ◽  
Arvind H. Jadhav
Keyword(s):  
Ionic Liquid ◽  
Room Temperature ◽  
Cycloaddition Reaction ◽  
Solvent Free ◽  
Alkyl Aryl ◽  
Mild Conditions ◽  
Solvent Free Conditions ◽  
Coupling Strategy ◽  
Multicomponent Coupling

A room temperature-based ionic liquid [bmim]Cl-catalyzed multicomponent coupling strategy for the synthesis of 3-alkylamino-2-alkyl/aryl/hetero-aryl indolizine-1-carbonitrile derivatives under mild conditions is shown.

scholarly journals Hydrostannylation-Cross-Coupling Strategy for the Stereoselective Synthesis of Alkylidenemalonates and Related α,β-Unsaturated Esters

2015 ◽  
Vol 2015 (6) ◽  
pp. 1264-1272 ◽  
Author(s):  
Shinichi Fujiwara ◽  
Romain Cadou ◽  
Yousuke Yamaoka ◽  
Kiyosei Takasu ◽  
Ken-ichi Yamada
Keyword(s):  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Unsaturated Esters ◽  
Coupling Strategy

Stereoselective Synthesis of 1,3-enynylselenides via Palladium-Catalysed Cross Coupling Reactions

2002 ◽  
Vol 2002 (8) ◽  
pp. 376-377 ◽  
Author(s):  
Ming-Zhong Cai ◽  
Chun-Yun Peng ◽  
Hong Zhao ◽  
Jia-Di Huang
Keyword(s):  
Room Temperature ◽  
Stereoselective Synthesis ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction

( E)-α-Bromovinylselenides undergo a cross coupling reaction with alkynyl Grignard reagents in the presence of tetrakis(triphenylphosphine)palladium(0) in THF at room temperature to afford 1,3-enynylselenides in good yields.

Pyrone-derived Marine Natural Products: A Review on Isolation, Bio-activities and Synthesis

2020 ◽  
Vol 24 (4) ◽  
pp. 354-401 ◽  
Author(s):  
Keisham S. Singh
Keyword(s):  
Natural Products ◽  
Marine Natural Products ◽  
Marine Fungi ◽  
Kojic Acid ◽  
Biological Activities ◽  
Biological Significance ◽  
Pyrone Ring ◽  
Enol Ethers ◽  
Bioactive Natural Products ◽  
Marine Metabolites

Marine natural products (MNPs) containing pyrone rings have been isolated from numerous marine organisms, and also produced by marine fungi and bacteria, particularly, actinomycetes. They constitute a versatile structure unit of bioactive natural products that exhibit various biological activities such as antibiotic, antifungal, cytotoxic, neurotoxic, phytotoxic and anti-tyrosinase. The two structure isomers of pyrone ring are γ- pyrone and α-pyrone. In terms of chemical motif, γ-pyrone is the vinologous form of α- pyrone which possesses a lactone ring. Actinomycete bacteria are responsible for the production of several α-pyrone compounds such as elijopyrones A-D, salinipyrones and violapyrones etc. to name a few. A class of pyrone metabolites, polypropionates which have fascinating carbon skeleton, is primarily produced by marine molluscs. Interestingly, some of the pyrone polytketides which are found in cone snails are actually synthesized by actinomycete bacteria. Several pyrone derivatives have been obtained from marine fungi such as Aspergillums flavus, Altenaria sp., etc. The γ-pyrone derivative namely, kojic acid obtained from Aspergillus fungus has high commercial demand and finds various applications. Kojic acid and its derivative displayed inhibition of tyrosinase activity and, it is also extensively used as a ligand in coordination chemistry. Owing to their commercial and biological significance, the synthesis of pyrone containing compounds has been given attention over the past years. Few reviews on the total synthesis of pyrone containing natural products namely, polypropionate metabolites have been reported. However, these reviews skipped other marine pyrone metabolites and also omitted discussion on isolation and detailed biological activities. This review presents a brief account of the isolation of marine metabolites containing a pyrone ring and their reported bio-activities. Further, the review covers the synthesis of marine pyrone metabolites such as cyercene-A, placidenes, onchitriol-I, onchitriol-II, crispatene, photodeoxytrichidione, (-) membrenone-C, lihualide-B, macrocyclic enol ethers and auripyrones-A & B.

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.

The Merger of CF3SO2Na and Palladium Catalysis to Enable Decarboxylative Cross-Coupling for the Synthesis of Aromatic Ketones under Room Temperature

2021 ◽  
Author(s):  
Pan Xie ◽  
Cheng Xue ◽  
Cancan Wang ◽  
Dongdong Du ◽  
Sanshan Shi
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Palladium Catalysis ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Aromatic Ketones ◽  
Aryl Ketones ◽  
Oxocarboxylic Acids

A CF3SO2Na/Pd(OAc)2 co-catalyzed strategy is developed to produce aryl ketones via visible-light-induced decarboxylative cross-coupling of α-oxocarboxylic acids and aryl boronic acids. This process was perfomed under air at room temperature,...

Sign in / Sign up

Export Citation Format

Share Document