General Synthetic Approach for the Laurencia Family of Natural Products Empowered by a Potentially Biomimetic Ring Expansion

2019 ◽  
Vol 141 (19) ◽  
pp. 7776-7788 ◽  
Author(s):  
Yu-An Zhang ◽  
Natalie Yaw ◽  
Scott A. Snyder
Keyword(s):  
Natural Products ◽  
Ring Expansion ◽  
Synthetic Approach

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

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

scholarly journals Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones

Catalysts ◽  
2019 ◽  
Vol 9 (1) ◽  
pp. 28 ◽  
Author(s):  
Alessandra Casnati ◽  
Elena Motti ◽  
Raffaella Mancuso ◽  
Bartolo Gabriele ◽  
Nicola Della Ca’
Keyword(s):  
Natural Products ◽  
Carbonyl Group ◽  
Ring Expansion ◽  
Catalytic Synthesis ◽  
Chiral Auxiliaries ◽  
Aziridine Ring ◽  
Urea Derivatives ◽  
Structural Motifs ◽  
Recent Advances ◽  
Direct Incorporation

2-Imidazolidinone and its analogues are omnipresent structural motifs of pharmaceuticals, natural products, chiral auxiliaries, and intermediates in organic syntheses. Over the years, continuous efforts have been addressed to the development of sustainable and more efficient protocols for the synthesis of these heterocycles. This review gives a summary of the catalytic strategies to access imidazolidin-2-ones and benzimidazolidin-2-ones that have appeared in the literature from 2010 to 2018. Particularly important contributions beyond the timespan will be mentioned. The review is organized in four main chapters that identify the most common approaches to imidazolidin-2-one derivatives: (1) the direct incorporation of the carbonyl group into 1,2-diamines, (2) the diamination of olefins, (3) the intramolecular hydroamination of linear urea derivatives and (4) aziridine ring expansion. Methods not included in this classification will be addressed in the miscellaneous section.

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.

scholarly journals Synthesis of Highly Functionalised Furo[3,4-b]pyrans: Towards the Fungal Metabolite (−)-TAN-2483B

2021 ◽  
Author(s):  
◽  
R.M. Kalpani K. Somarathne
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Cyclopropane Ring ◽  
Ring Expansion ◽  
Ethyl Esters ◽  
Pyran Ring ◽  
Synthetic Strategy ◽  
Alternative Approach ◽  
Synthetic Approaches

<p>Carbohydrate-derived cyclopropanes combine both the stereochemical wealth of carbohydrates and the reactivity of cyclopropanes. A diverse variety of reaction modes for these cyclopropyl carbohydrates can be harnessed for the synthesis of natural products and other targets.  The natural products (−)-TAN-2483A and (−)-TAN-2483B are fungal secondary metabolites displaying a variety of bioactivities such as inhibition of c-src kinase action and parathyroid hormone-induced bone resorption. This thesis described several synthetic approaches to the natural product (−)-TAN-2483B and analogues of (−)-TAN-2483B employing cyclopropane ring expansion.  The synthetic route to (−)-TAN-2483B began with the readily available substrate D-mannose. The pyran ring unsaturation of the natural product was established by a cyclopropanation-ring expansion sequence. A synthetic strategy via dichlorocyclopropane-based intermediates is described in chapter 2. This being unsuccessful, an alternative approach via 2-fomyl-glycal was developed in chapter 3. The chapter 2 and 3 provided a solid background for the achievement of the analogues synthesis illustrated in chapter 4 via dibromocyclopropane. Lewis acid-mediated alkynylation followed by Pdcatalysed carbonylative lactonisation was successfully utilised in the revelation of the furo[3,4-b]pyran ring skeleton. This route afforded analogues of TAN-2483B; the Z-and E-unsaturated ethyl esters 140 and 141 and hydroxy(−)-TAN-2483B 145. The total synthesis of (−)-TAN-2483B was not achieved due to unforeseen obstacles encountered in the deoxygenation of the side arm of 335 (Chapter 4) into the E-propenyl side arm of (−)-TAN-2483B.</p>

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.

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