Progress Toward the Total Synthesis of the Epoxyquinoid Family of Natural Products PDF Download
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Author: Publisher: ISBN: Category : Languages : en Pages : 228
Book Description
Enyne metathesis is a powerful C-C bond forming reaction that combines an alkene and an alkyne and forms a conjugated 1,3-diene. The scope of enyne metathesis was expanded by combining various alkynes with vinyl ethers. Typically vinyl ethers are poor metathesis substrates, but a method was developed for the synthesis of dienol ethers utilizing ruthenium carbenes. The products of these reactions were subjected to [4+2] cycloaddition conditions to give substituted cyclohexene rings. The epoxyquinoid family is a highly targeted series of natural products. A general method for the synthesis of the core structure of these natural products has been explored. An enyne cross metathesis/ring closing metathesis step was designed as the key reaction to this synthesis. A Darzen's condensation between a chiral [alpha]-alkoxy aldehyde and a chloroacyl oxazolidinone was successfully employed to join two fragments of the molecule as well as to install an epoxide. A highly diastereoselective cuprate addition set the stereochemistry of the first stereogenic center. The early intermediates were prepared via easily scalable organic syntheses procedures including utilizing a carbohydrate as the source of chirality. Ring closing enyne metathesis to form the epoxyquinoid core was evaluated in two epimeric series.
Author: Publisher: ISBN: Category : Languages : en Pages : 228
Book Description
Enyne metathesis is a powerful C-C bond forming reaction that combines an alkene and an alkyne and forms a conjugated 1,3-diene. The scope of enyne metathesis was expanded by combining various alkynes with vinyl ethers. Typically vinyl ethers are poor metathesis substrates, but a method was developed for the synthesis of dienol ethers utilizing ruthenium carbenes. The products of these reactions were subjected to [4+2] cycloaddition conditions to give substituted cyclohexene rings. The epoxyquinoid family is a highly targeted series of natural products. A general method for the synthesis of the core structure of these natural products has been explored. An enyne cross metathesis/ring closing metathesis step was designed as the key reaction to this synthesis. A Darzen's condensation between a chiral [alpha]-alkoxy aldehyde and a chloroacyl oxazolidinone was successfully employed to join two fragments of the molecule as well as to install an epoxide. A highly diastereoselective cuprate addition set the stereochemistry of the first stereogenic center. The early intermediates were prepared via easily scalable organic syntheses procedures including utilizing a carbohydrate as the source of chirality. Ring closing enyne metathesis to form the epoxyquinoid core was evaluated in two epimeric series.
Author: Shinsuke Inuki Publisher: Springer Science & Business Media ISBN: 4431540431 Category : Science Languages : en Pages : 115
Book Description
The author has developed novel methodologies for highly efficient construction of functionalized heterocycles by palladium-catalyzed domino/cascade cyclization of allenes and related compounds containing appropriate nucleophilic group(s). Based on these methodologies, enantioselective total syntheses of bioactive natural products, pachastrissamine (26% overall yield in seven steps), lysergic acid (4.0% overall yield in fifteen steps), lysergol (3.6% overall yield in fifteen steps) and isolysergol (8.2% overall yield in eleven steps) have been achieved. These are more facile synthetic route than those previously reported. These findings would contribute to the development of efficient synthetic methods for biologically active compounds containing a complex structure.
Author: John ApSimon Publisher: John Wiley & Sons ISBN: 0470129506 Category : Science Languages : en Pages : 618
Book Description
Each volume reviews the total synthesis of a set of compounds looking at syntheses reported historically and at the practice current at the time of publication. From volume 1 focusing on carbohydrates, prostagladins, nucleic acids, antibiotics, naturally occurring oxygen ring compounds and pyrrole pigments, the series continues with coverage of aromatic steroids, monoterpenes, triterpenes, sesquiterpenes, cannabinoids, natural inophores, insect pheromones and alkaloids. Volumes revisit the total synthesis of key compounds such as carbohydrates, nucleic acids and pyrrole pigments several times during the series building a picture of the historic development of total synthesis techniques for these major groups. Chapters are edited by experts in their field to give a complete overview of the best in the field at the time.
Author: John ApSimon Publisher: Wiley-Interscience ISBN: 0470129573 Category : Science Languages : en Pages : 304
Book Description
The Total Synthesis of Natural Products, Volume Four Edited by John ApSimon The fourth volume in this successful series offers synthetic approaches to a wide variety of natural products, including the synthesis of cannabinoids, natural inophores, insect pheromones, monoterpenes, and prostaglandins. 1981 610 pp. The Total Synthesis of Natural Products, Volume Five Edited by John ApSimon In this fifth volume, ApSimon presents a review by Heathcock and co-workers covering the total synthesis of sesquiterpenes published during 1970-1979, offering an overview of current practice in synthesis. 1983 550 pp.
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Author: Stephen Hanessian
Author: Meredeth Ann McGowan
Author: Masahisa Nakada
Author: Shinsuke Inuki
Author: 
Author: John ApSimon
Author: John ApSimon
Author: Douglas D. McLeod
Author: James Anthony Schwindeman