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Your search keyword '"Keto Acid"' showing total 17 results
Start Over Descriptor "Keto Acid" Publisher american chemical society (acs)
17 results on '"Keto Acid"'

1. Bicyclic- and Tricyclic-β-lactones via Organonucleophile-Promoted Bis-Cyclizations of Keto Acids: Enantioselective Synthesis of (+)-Dihydroplakevulin

Author

Huda Henry‐Riyad, Changsuk Lee, Daniel Romo, and Vikram C. Purohit

Subjects
Models, Molecular, chemistry.chemical_classification, Bicyclic molecule, Stereochemistry, Organic Chemistry, Enantioselective synthesis, Stereoisomerism, Cyclopentanes, Crystallography, X-Ray, Keto Acids, Biochemistry, Aldehyde, Cycloaddition, Lactones, Aldol reaction, chemistry, Cyclization, Keto acid, Physical and Theoretical Chemistry, Tricyclic
Abstract

A highly diastereoselective, nucleophile-promoted bis-cyclization process, employing readily available and tractable keto acid substrates, is described. This methodology provides concise access to bicyclic- and tricyclic-beta-lactones bearing tertiary carbinol centers and quaternary carbons, greatly extending the scope of previous routes to bicyclic-beta-lactones from aldehyde acid substrates. The utility of the method was demonstrated by application to an enantioselective synthesis of (+)-dihydroplakevulin A. This and related processes may be revealing a subtle interplay between [2+2] cycloaddition and nucleophile-catalyzed aldol lactonization (NCAL) reaction manifolds.

Published
2006

2. Synthetic Pathways to 2,2-Dimethyl-6-oxo-1-cyclohexaneacetic Acid, a Useful Isoprenoid Building Block

Author

Lucjan Strekowski,†,‡ and, Zdzislaw Paryzek, and Merle A. Battiste

Subjects
chemistry.chemical_compound, Ethyl bromoacetate, Hydrolysis, Mesityl oxide, Chemistry, Cyclohexaneacetic acid, Yield (chemistry), Organic Chemistry, Organic chemistry, Keto acid, Physical and Theoretical Chemistry, Alkylation, Terpenoid
Abstract

Six new synthetic routes to 2,2-dimethyl-6-oxo-1-cyclohexaneacetic acid (1) from readily available starting materials have been evaluated. The most efficient method (yield 35%) involves alkylation of Hagemann's ester with ethyl bromoacetate followed by hydrolysis of the resultant ethyl 3-(ethoxycarbonyl)-2-methyl-6-oxo-1-cyclohexeneacetate to unsaturated keto acid 2-methyl-6-oxo-1-cyclohexeneacetic acid (19) and then treatment of 19 with Me2CuLi. A method from mesityl oxide is longer and slightly less efficient (30%). These two methods are suitable for a large-scale preparation of 1.

Published
1997

3. Novel N1−C4 β-Lactam Bond Breakage. Synthesis of Enantiopure α-Alkoxy-γ-keto Acid Derivatives

Author

Maria C. Redondo, Pedro Almendros, and Benito Alcaide

Subjects
Addition reaction, Trimethylsilyl, Chemistry, Stereochemistry, Organic Chemistry, Alpha (ethology), General Medicine, Biochemistry, chemistry.chemical_compound, Enantiopure drug, Breakage, Lactam, polycyclic compounds, Alkoxy group, Keto acid, Physical and Theoretical Chemistry, Thiazole
Abstract

Addition reaction of 2-(trimethylsilyl)thiazole (TMST) to cis- or trans-4-formyl-β-lactams gave enantiopure α-alkoxy-γ-keto acid derivatives via a novel N1−C4 bond breakage of the β-lactam nucleus....

Published
2004

8. Synthesis of cyclic acylated enamino ester dipeptide analogs via the bromolactonization of a keto acid phosphorane

Author

Andrew D. Abell and Jane M. Taylor

Subjects
chemistry.chemical_classification, chemistry.chemical_compound, Dipeptide, chemistry, Stereochemistry, Organic Chemistry, lipids (amino acids, peptides, and proteins), Keto acid, Phosphorane, Enol, Amino acid
Abstract

The acylated cyclic enamino ester dipeptide analogues 12, 13, and 17-10 have been prepared via lactonization of the keto acid phosphorane 8 followed by incorporation of an amino acid into the product enol lactones

Published
1993

17. THE STABILITY OF THE KETO ACID FROM METHIONINE

Author

Heinrich Waelsch and Ernest Borek

Subjects
chemistry.chemical_compound, Colloid and Surface Chemistry, Methionine, chemistry, Organic chemistry, General Chemistry, Keto acid, Biochemistry, Catalysis
Published
1939

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