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Your search keyword '"Sergio G. Duron"' showing total 4 results
Start Over Author "Sergio G. Duron" Topic general chemistry
4 results on '"Sergio G. Duron"'

1. Annulation of Thioimidates and Vinyl Carbodiimides to Prepare 2-Aminopyrimidines, Competent Nucleophiles for Intramolecular Alkyne Hydroamination. Synthesis of (−)-Crambidine

Author

Nicholas R. Perl, Sergio G. Duron, David Y. Gin, Sudeep Prajapati, Hahdi H. Perfect, and Nathan D. Ide

Subjects
chemistry.chemical_classification, Annulation, Convergent synthesis, Alkyne, Stereoisomerism, General Chemistry, Biochemistry, Catalysis, Article, Carbodiimides, Colloid and Surface Chemistry, Pyrimidines, Nucleophile, chemistry, Intramolecular force, Alkynes, Imidoesters, Organic chemistry, Spiro Compounds, Hydroamination, Amination, Guanidine
Abstract

A convergent synthesis of (−)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.

Published
2010

2. Total synthesis of (+)-batzelladine A and (-)-batzelladine D via [4 + 2]-annulation of vinyl carbodiimides with N-alkyl imines

Author

Michael Arnold, Sergio G. Duron, David Y. Gin, and Kenneth A. Day

Subjects
chemistry.chemical_classification, Annulation, Intramolecular reaction, Stereochemistry, Imine, Total synthesis, Stereoisomerism, General Chemistry, Biochemistry, Guanidines, Catalysis, Article, chemistry.chemical_compound, Carbodiimides, Colloid and Surface Chemistry, Polycyclic compound, Alkaloids, Pyrimidines, chemistry, Intramolecular force, Stereoselectivity, Imines, Amination
Abstract

A diastereoselective [4 + 2]-annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as long-range directed hydrogenation and diastereoselective intramolecular iodo-amination, led to highly convergent total syntheses of (-)-batzelladine D and (+)-batzelladine A with excellent stereocontrol.

Published
2006

3. Sulfide-mediated dehydrative glycosylation

Author

Hien M. Nguyen, David Y. Gin, Sergio G. Duron, and Yanning Chen

Subjects
chemistry.chemical_classification, Anomer, Glycosylation, Sulfide, Sulfonium, Oligosaccharides, Water, General Chemistry, Sulfides, Biochemistry, Combinatorial chemistry, Catalysis, carbohydrates (lipids), chemistry.chemical_compound, Colloid and Surface Chemistry, chemistry, Nucleophile, Reagent, Safrole, lipids (amino acids, peptides, and proteins), Glycosyl, Oxidation process, Glycoconjugates, Oxidation-Reduction
Abstract

The development of a new method for glycosylation with 1-hydroxy glycosyl donors employing dialkyl sulfonium reagents is described. The process employs the reagent combination of a dialkyl sulfide and triflic anhydride to effect anomeric bond constructions. This controlled dehydrative coupling of various C(1)-hemiacetal glycosyl donors and nucleophilic acceptors proceeds by way of a sulfide-to-sulfoxide oxidation process in which triflic anhydride serves as the oxidant.

Published
2001

4. Diastereoselective [4+2] Annulation of Vinyl Carbodiimides with N-Alkyl Imines. Asymmetric Synthetic Access to the Batzelladine Alkaloids

Author

David Y. Gin, Michael Arnold, and Sergio G. Duron

Subjects
Annulation, Vinyl Compounds, Alkylation, Stereochemistry, Guanidines, Biochemistry, Catalysis, Stereocenter, chemistry.chemical_compound, Alkaloids, Colloid and Surface Chemistry, Organic chemistry, Guanidine, Alkyl, chemistry.chemical_classification, Natural product, Chemistry, Enantioselective synthesis, Stereoisomerism, General Medicine, Batzelladine D, General Chemistry, Carbodiimides, Pyrimidines, Intramolecular force, Stereoselectivity, Organic synthesis, Imines
Abstract

A diastereoselective [4+2] annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich tricyclic core of the batzelladine alkaloids. Its application to the asymmetric synthesis of batzelladine D permitted the use of long-range, directed hydrogenation and stereoselective intramolecular iodoamination as additional key steps to establish the remaining stereocenters within the natural product with excellent stereocontrol.

Published
2005
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