scholarly journals All-carbon [3 + 2] cycloaddition in natural product synthesis

2020 ◽  
Vol 16 ◽  
pp. 3015-3031
Author(s):  
Zhuo Wang ◽  
Junyang Liu
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Structural Features ◽  
Single Step ◽  
Natural Product Synthesis ◽  
Synthetic Chemistry ◽  
Quaternary Centers ◽  
Chemical Structures ◽  
Quaternary Center ◽  
Medicinal Properties

Many natural products possess interesting medicinal properties that arise from their intriguing chemical structures. The highly-substituted carbocycle is one of the most common structural features in many structurally complicated natural products. However, the construction of highly-substituted, stereo-congested, five-membered carbocycles containing all-carbon quaternary center(s) is, at present, a distinct challenge in modern synthetic chemistry, which can be accessed through the all-carbon [3 + 2] cycloaddition. More importantly, the all-carbon [3 + 2] cycloaddition can forge vicinal all-carbon quaternary centers in a single step and has been demonstrated in the synthesis of complex natural products. In this review, we present the development of all-carbon [3 + 2] cycloadditions and illustrate their application in natural product synthesis reported in the last decade covering 2011–2020 (inclusive).

scholarly journals Facilitating Biomimetic Syntheses of Borrerine Derived Alkaloids by Means of Flow-Chemical Methods

2015 ◽  
Vol 68 (4) ◽  
pp. 693 ◽  
Author(s):  
Sonja B. Kamptmann ◽  
Steven V. Ley
Keyword(s):  
Natural Product ◽  
Flow Chemistry ◽  
Single Step ◽  
Natural Product Synthesis ◽  
Biomimetic Synthesis ◽  
Synthetic Chemistry ◽  
Chemical Methods ◽  
Complex Architectures

Flow chemistry is widely used nowadays in synthetic chemistry and has increasingly been applied to complex natural product synthesis. However, to date flow chemistry has not found a place in the area of biomimetic synthesis. Here we show the syntheses of borrerine derived alkaloids, indicating that we can use biomimetic principles in flow to prepare complex architectures in a single step.

Unzipping Natural Products: Improved Natural Product Structure Predictions by Ensemble Modeling and Fingerprint Matching

2018 ◽  
Author(s):  
William A. Shirley ◽  
Brian P. Kelley ◽  
Yohann Potier ◽  
John H. Koschwanez ◽  
Robert Bruccoleri ◽  
...  
Keyword(s):  
Natural Products ◽  
Open Source ◽  
Natural Product ◽  
Gene Cluster ◽  
Public Domain ◽  
Product Structure ◽  
Fingerprint Matching ◽  
Ensemble Modeling ◽  
Chemical Structures ◽  
Source Gene

This pre-print explores ensemble modeling of natural product targets to match chemical structures to precursors found in large open-source gene cluster repository antiSMASH. Commentary on method, effectiveness, and limitations are enclosed. All structures are public domain molecules and have been reviewed for release.

Recent applications of asymmetric organocatalytic annulation reactions in natural product synthesis

2021 ◽  
Author(s):  
Nengzhong Wang ◽  
Zugen Wu ◽  
Junjie Wang ◽  
Nisar Ullah ◽  
Yixin Lu
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Natural Products Synthesis

A comprehensive and updated summary of asymmetric organocatalytic annulation reactions is presented; in particular, the applications of these annulation strategies to natural products synthesis are highlighted.

scholarly journals Applications of the Horner-Wadsworth-Emmons olefination in modern natural product synthesis

Synthesis ◽  
2021 ◽  
Author(s):  
Dávid Roman ◽  
Maria Sauer ◽  
Christine Beemelmanns
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Reaction Conditions ◽  
Comprehensive Review ◽  
Modern Natural ◽  
Key Steps ◽  
Synthetic Approaches

Here, we have summarized more than 30 representative natural product syntheses published in 2015 to 2020 that employ one or more Horner-Wadsworth-Emmons (HWE) reactions. We comprehensively describe the applied phosphonate reagents, HWE reaction conditions and key steps of the total synthetic approaches. Our comprehensive review will support future synthetic approaches and serve as guideline to find the best HWE conditions for the most complicated natural products known

scholarly journals Diverse Taxonomies for Diverse Chemistries: Enhanced Representation of Natural Product Metabolism in UniProtKB

Metabolites ◽  
2021 ◽  
Vol 11 (1) ◽  
pp. 48
Author(s):  
Marc Feuermann ◽  
Emmanuel Boutet ◽  
Anne Morgat ◽  
Kristian Axelsen ◽  
Parit Bansal ◽  
...  
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Semantic Web Technologies ◽  
Knowledge Resources ◽  
Web Technologies ◽  
Chemical Structures ◽  
Biological Interest ◽  
Catalyzed Reactions ◽  
Enzyme Catalyzed Reactions ◽  
Practical Demonstration

The UniProt Knowledgebase UniProtKB is a comprehensive, high-quality, and freely accessible resource of protein sequences and functional annotation that covers genomes and proteomes from tens of thousands of taxa, including a broad range of plants and microorganisms producing natural products of medical, nutritional, and agronomical interest. Here we describe work that enhances the utility of UniProtKB as a support for both the study of natural products and for their discovery. The foundation of this work is an improved representation of natural product metabolism in UniProtKB using Rhea, an expert-curated knowledgebase of biochemical reactions, that is built on the ChEBI (Chemical Entities of Biological Interest) ontology of small molecules. Knowledge of natural products and precursors is captured in ChEBI, enzyme-catalyzed reactions in Rhea, and enzymes in UniProtKB/Swiss-Prot, thereby linking chemical structure data directly to protein knowledge. We provide a practical demonstration of how users can search UniProtKB for protein knowledge relevant to natural products through interactive or programmatic queries using metabolite names and synonyms, chemical identifiers, chemical classes, and chemical structures and show how to federate UniProtKB with other data and knowledge resources and tools using semantic web technologies such as RDF and SPARQL. All UniProtKB data are freely available for download in a broad range of formats for users to further mine or exploit as an annotation source, to enrich other natural product datasets and databases.

14 Electrochemistry in Natural Product Synthesis

2022 ◽  
Author(s):  
K. Lam ◽  
M. C. Leech ◽  
A. J. J. Lennox
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Redox Reactions ◽  
Natural Product Synthesis ◽  
Reaction Type ◽  
Multistep Synthesis ◽  
Reaction Solution ◽  
Electrochemical Redox ◽  
Synthetic Methodologies ◽  
Unique Ability

The multistep synthesis of natural products has historically served as a useful and informative platform for showcasing the best, state-of-the-art synthetic methodologies and technologies. Over the last several decades, electrochemistry has proved itself to be a useful tool for conducting redox reactions. This is primarily due to its unique ability to selectively apply any oxidizing or reducing potential to a sufficiently conductive reaction solution. Electrochemical redox reactions are readily scaled and can be more sustainable than competing strategies based on conventional redox reagents. In this chapter, we summarize the examples where electrochemistry has been used in the synthesis of natural products. The chapter is organized by the reaction type of the electrochemical step and covers both oxidative and reductive reaction modes.

scholarly journals Catalytic Asymmetric Intramolecular Darzens Reaction of 2-Halomalonate Derivatives

2019 ◽  
Vol 14 (10) ◽  
pp. 1934578X1988440
Author(s):  
Kenichi Kobayashi ◽  
Kosaku Tanaka ◽  
Momoko Suzuki ◽  
Hiroshi Kogen
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Phase Transfer ◽  
Building Blocks ◽  
Natural Product Synthesis ◽  
Darzens Reaction ◽  
Phase Transfer Catalysts ◽  
Catalytic Asymmetric

A catalytic asymmetric intramolecular Darzens reaction of 2-halomalonate derivatives was developed for the enantioselective preparation of chiral building blocks for epoxide-containing natural products. Among the screened catalysts, some phase-transfer catalysts gave the desired epoxide in moderate enantioselectivity, albeit in low yield. The epoxide product would be useful as versatile chiral building blocks for natural product synthesis.

scholarly journals Directed aromatic functionalization in natural-product synthesis: Fredericamycin A, nothapodytine B, and topopyrones B and D

2011 ◽  
Vol 7 ◽  
pp. 1475-1485 ◽  
Author(s):  
Charles Dylan Turner ◽  
Marco A Ciufolini
Keyword(s):  
Natural Products ◽  
Biological Activity ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Fredericamycin A

This is a review of our efforts toward the synthesis of a group of natural products that display noteworthy biological activity: Fredericamycin A, nothapodytine B, and topopyrones B and D. In each case, directed aromatic functionalization methodology greatly facilitated the assembly of the key molecular subunits.

Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications

Synthesis ◽  
2020 ◽  
Vol 52 (14) ◽  
pp. 1991-2007 ◽  
Author(s):  
Alison J. Frontier ◽  
Shukree Abdul-Rashed ◽  
Connor Holt
Keyword(s):  
Natural Products ◽  
Small Molecules ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Pericyclic Reactions ◽  
Prins Reaction ◽  
Prins Cyclization ◽  
Synthetic Utility ◽  
Cascade Processes ◽  
Saturated Heterocycles

This review focuses on alkynyl Prins and alkynyl aza-Prins cyclization­ processes, which involve intramolecular coupling of an alkyne with either an oxocarbenium or iminium electrophile. The oxocarbenium or iminium species can be generated through condensation- or elimination-type processes, to achieve an overall bimolecular annulation that enables the synthesis of both oxygen- and nitrogen-containing­ saturated heterocycles with different ring sizes and substitution patterns. Also discussed are cascade processes in which alkynyl Prins heterocyclic adducts react to trigger subsequent pericyclic reactions, including [4+2] cycloadditions and Nazarov electrocyclizations, to rapidly construct complex small molecules. Finally, examples of the use of alkynyl Prins and alkynyl aza-Prins reactions in the synthesis of natural products are described. The review covers the literature through the end of 2019.1 Introduction1.1 Alkyne-Carbonyl Coupling Pathways1.2 Coupling/Cyclization Cascades Using the Alkynyl Prins Reaction2 Alkynyl Prins Annulation (Oxocarbenium Electrophiles)2.1 Early Work2.2 Halide as Terminal Nucleophile2.3 Oxygen as Terminal Nucleophile2.4 Arene as Terminal Nucleophile (Intermolecular)2.5 Arene Terminal Nucleophile (Intramolecular)2.6 Cyclizations Terminated by Elimination3 Synthetic Utility of Alkynyl Prins Annulation3.1 Alkynyl Prins-Mediated Synthesis of Dienes for a [4+2] Cyclo­- addition­-Oxidation Sequence3.2 Alkynyl Prins Cyclization Adducts as Nazarov Cyclization Precursors3.3 Alkynyl Prins Cyclization in Natural Product Synthesis4 Alkynyl Aza-Prins Annulation4.1 Iminium Electrophiles4.2 Activated Iminium Electrophiles5 Alkynyl Aza-Prins Cyclizations in Natural Product Synthesis6 Summary and Outlook

scholarly journals Bridging the gap between natural product synthesis and drug discovery

2020 ◽  
Vol 37 (11) ◽  
pp. 1436-1453 ◽  
Author(s):  
Nathanyal J. Truax ◽  
Daniel Romo
Keyword(s):  
Natural Products ◽  
Drug Discovery ◽  
Natural Product ◽  
Chemical Space ◽  
Natural Product Synthesis ◽  
Chemical Information

Various synthetic strategies have been developed to explore natural products as an enduring source of chemical information useful for probing biological relevant chemical space and impacting drug discovery.

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