scholarly journals Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G

2016 ◽  
Vol 12 ◽  
pp. 2689-2693 ◽  
Author(s):  
Youngeun Jung ◽  
Dileep Kumar Singh ◽  
Ikyon Kim
Keyword(s):  
Natural Products ◽  
Suzuki Coupling ◽  
Synthetic Approach ◽  
Sonogashira Coupling ◽  
Cyclization Reactions ◽  
Aryl Ring ◽  
Rapid Access ◽  
Alkoxy Groups

The recognition of the local symmetric image within benzofuran-based natural oligostilbenoids guided us to design a modular synthetic approach to these molecules by utilizing a three-step sequence consisting of Sonogashira coupling, iodocyclization, and Suzuki coupling. During our synthesis, the relative reactivities of ester, aldehyde, and alkoxy groups on the same aryl ring toward the neighboring alkyne in the iodine-mediated cyclization reactions were explored. Starting from the symmetrical 3,5-dimethoxybenzyl alcohol, this route allowed rapid access to 2,3-diarylbenzofuran, a key intermediate to several oligostilbenoid natural products, in good overall yields.

Intramolecular Diels–Alder Reactions of Oxazoles, Imidazoles, and Thiazoles

Synthesis ◽  
2020 ◽  
Author(s):  
Peter Wipf ◽  
Thanh T. Nguyen
Keyword(s):  
Natural Products ◽  
Lewis Acid ◽  
Acid Catalysis ◽  
Copper Catalysts ◽  
Diels Alder ◽  
Synthetic Approach ◽  
Highly Efficient ◽  
Intramolecular Cycloadditions ◽  
Western Segment ◽  
Target Molecules

AbstractThe development of the intramolecular Diels–Alder cycloaddition­ of azole heterocycles, i.e. oxazoles (IMDAO), imidazoles (IMDAI), and thiazoles (IMDAT), has had a significant impact on the efficient preparation of heterocyclic intermediates and natural products. In particular, highly efficient and versatile IMDAO reactions have been utilized as a key step in several synthetic schemes to provide alkaloids and terpenoid target molecules. More limited studies have been performed on IMDAI and IMDAT cycloadditions. Some drawbacks, such as the occasionally­ challenging preparation of IMDA precursors, are also highlighted in this review. Perspectives are provided on how IMDAI and IMDAT­ transformations can be further expanded for target-directed syntheses.1 Introduction2 Oxazoles2.1 IMDAO Approaches to Furanosesquiterpenes and Furanosteroids2.1.1 Syntheses of Highly Oxygenated Sesquiterpenes2.1.2 Syntheses of (±)-Gnididione and (±)-Isognididione2.1.3 Synthesis of (±)-Stemoamide2.1.4 Synthesis of (±)-Paniculide A2.1.5 Syntheses of (+)- and (–)-Norsecurinine2.1.6 Synthesis of Evodone2.1.7 Syntheses of (±)-Ligularone and (±)-Petasalbine2.1.8 Syntheses of Imerubrine, Isoimerubrine, and Grandirubrine2.1.9 Syntheses of Furanosteroids2.1.10 Syntheses of Substituted Indolines and Tetrahydroquinolines2.2 IMDAO Approaches to Pyridines: the Kondrat’eva Reaction2.2.1 Syntheses of Suaveoline and Norsuaveoline2.2.2 Synthesis of Eupolauramine2.2.3 Syntheses of (–)-Plectrodorine and (+)-Oxerine2.2.4 Synthesis of Amphimedine2.2.5 Synthetic Approach to the Western Segment of Haplophytine2.2.6 Synthesis of Marinoquinoline A2.2.6.1 IMDAO Approach to Marinoquinoline A2.2.6.2 Scope of Allenyl IMDAO Cycloaddition2.3 Lewis Acid Catalysis in IMDAO Reactions2.3.1 Effects of Europium Catalysts on IMDAO Reactions2.3.2 Effects of Copper Catalysts on IMDAO Reactions3 Imidazoles 4 Thiazoles4.1 Syntheses of Menthane and Eremophilane4.2 Further Comments on the Intramolecular Cycloadditions of Thiocarbonyl Ylides5 Conclusions and Outlook

ChemInform Abstract: Eight Membered Ethers via Diene Metathesis: Synthetic Approach to Laureatin Natural Products.

ChemInform ◽  
2010 ◽  
Vol 30 (33) ◽  
pp. no-no
Author(s):  
Simon D. Edwards ◽  
Terence Lewis ◽  
Richard J. K. Taylor
Keyword(s):  
Natural Products ◽  
Synthetic Approach ◽  
Diene Metathesis

scholarly journals Novel synthesis of furancarboxylate derivatives via cyclization reactions of (E)-ethyl 3-aryl-2-cyanoacrylates and ethyl glycinate hydrochloride

2020 ◽  
pp. 174751982095959
Author(s):  
Naili Luo ◽  
Shan Wang ◽  
Zhenjie Su ◽  
Cunde Wang
Keyword(s):  
Synthetic Approach ◽  
Cyclization Reactions ◽  
X Ray ◽  
X Ray Crystallography ◽  
Mild Conditions ◽  
Novel Synthesis ◽  
Substituted Furans

An efficient synthetic approach for the preparation of densely substituted furans starting from ( E)-ethyl 3-aryl-2-cyanoacrylates and ethyl glycinate hydrochloride mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene in the presence of water is investigated. The reactions are carried out under mild conditions in N,N-dimethylformamide at 95 °C. The products are cleanly obtained in 50%–57% yields, resulting in an appealing alternative for accessing polysubstituted furan-2,4-dicarboxylates. The structure of a typical product, diethyl 5-amino-3-( p-tolyl)furan-2,4-dicarboxylate, is confirmed by X-ray crystallography.

scholarly journals Chiral cyclopentadienyl RhIII-catalyzed enantioselective cyclopropanation of electron-deficient olefins enable rapid access to UPF-648 and oxylipin natural products

2019 ◽  
Vol 10 (9) ◽  
pp. 2773-2777 ◽  
Author(s):  
Coralie Duchemin ◽  
Nicolai Cramer
Keyword(s):  
Natural Products ◽  
Rapid Access

Chiral cyclopentadienyl-RhIII complexes catalyze enantioselective cyclopropanations of electron-deficient olefins with N-enoxysuccinimides and are used for syntheses of oxylipins and UPF-648.

Synthetic approach to seco-tetracenomycin natural products saccharothrixone A–C

2018 ◽  
Vol 59 (20) ◽  
pp. 1970-1973
Author(s):  
Bhavani Shankar Chinta ◽  
Harikrishna Sanapa ◽  
Kamala Prasad Vasikarla ◽  
Beeraiah Baire
Keyword(s):  
Natural Products ◽  
Synthetic Approach

From natural products to biological tools

2007 ◽  
Vol 79 (4) ◽  
pp. 753-761 ◽  
Author(s):  
Peter Wipf ◽  
Thomas H. Graham ◽  
Jingbo Xiao
Keyword(s):  
Natural Products ◽  
Therapeutic Potential ◽  
Reactive Oxygen ◽  
Synthetic Approach ◽  
Oxygen Scavenger

The development of a total synthetic approach for the antimitotic disorazole C1 and the design of a peptide isostere linked to the reactive oxygen scavenger 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) demonstrate established as well as novel strategies for mining the therapeutic potential of natural products.

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.

New methods for the synthesis of certain alkaloids and terpenoids

2011 ◽  
Vol 83 (3) ◽  
pp. 411-423 ◽  
Author(s):  
Martin G. Banwell ◽  
Anna L. Lehmann ◽  
Rajeev S. Menon ◽  
Anthony C. Willis
Keyword(s):  
Natural Products ◽  
Cyclization Reactions ◽  
New Methods

The use of ring-fused gem-dihalocyclopropanes, Au(I)-catalyzed cyclization reactions, and chemoenzymatic techniques in the synthesis of natural products is described.

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