Stereoselective Synthesis of 3-Hydroxyproline Benzyl Esters from <i>N</i>-Protected β-Aminoaldehydes and Benzyl Diazoacetate

Angle, Steven R.; Belanger, Dominique S.

doi:10.1021/jo030360f

Cited by 22 publications

(10 citation statements)

References 15 publications

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“…Angle and co-workers reported the total synthesis of indolizidine and pyrrolizidine alkaloids based on the method for the diastereoselective preparation of 3-hydroxyproline benzyl esters reported by the same group previously . The key proline intermediate was prepared as a single diastereomer by the reaction between protected α-hydroxy-β-aminoaldehyde 210 - 1 with benzyl diazoacetate in the presence of Lewis acid (BF 3 ·Et 2 O) (Scheme ).…”

Section: Miscellaneous Methodsmentioning

confidence: 99%

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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The main objective of this review is to provide a comprehensive survey of methods used for stereoselective construction of carbon-nitrogen bonds during the total synthesis of nitrogen-containing natural products that have appeared in the literature since 2000. The material is organized by specific reaction in order of decreasing number of applications in natural product synthesis. About 800 total syntheses of natural products with stereogenic carbon-nitrogen bonds described since 2000 have been reviewed.

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Section: Miscellaneous Methodsmentioning

confidence: 99%

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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“…The chiral atom C11 is in an S configuration. The bond distances and angles within this structure are in the normal ranges (Angle & Belanger, 2004;Van Esseveldt et al, 2003).…”

Section: Commentmentioning

confidence: 75%

1-(p-Tolylsulfonyl)-L-proline ethyl ester

Chen

Cui

et al. 2005

Acta Cryst E

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“…Due to its unique structural properties, proline (the only natural cyclic amino acid, presenting a pyrrolidine ring with conformational restrictions) has an important role in biological processes and peptide folding. In order to improve the efficacy and/or the structure for higher receptor recognition and selectivity, several research groups have developed proline mimics. − …”

Section: Conformational Studiesmentioning

confidence: 99%

Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides

et al. 2016

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Unnatural α-amino acids form a family of essential molecules used for, among other applications, the synthesis of modified peptides, to improve resistance to proteolytic enzyme degradation, and to modulate physico- and biochemical properties of bioactive peptides as well as chiral inducers in asymmetric synthesis. Among them, silicon-containing unnatural amino acids are becoming an interesting new class of building blocks. The replacement of carbon atoms in bioactive substances with silicon is becoming increasingly popular. Peptides containing silyl amino acids hold great promise for maintaining or reinforcing the biological activity of active compounds, while they simultaneously enhance their resistance to enzyme degradation. In addition, the lipophilicity of the silicon atom facilitates their membrane crossing and their bioavailability. Nowadays, the interest of the pharmaceutical industry in peptide- and protein-based therapies is increasing. In this respect, silicon-containing amino acids and peptides are likely to be a significant part of future innovations in this area, and more generally in the area of biomolecules. In this process, commercial availability of silicon-containing amino acids is necessary: new syntheses have been developed, and work in this area is ongoing. This review aims to be a comprehensive and general summary of the different methods used to prepare silicon-containing amino acids and their implications on conformational structures and biological applications when they are incorporated into bioactive molecules.

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Stereoselective Synthesis of 3-Hydroxyproline Benzyl Esters from N-Protected β-Aminoaldehydes and Benzyl Diazoacetate

Cited by 22 publications

References 15 publications

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

1-(p-Tolylsulfonyl)-L-proline ethyl ester

Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides

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