Advanced search
1 file | 1.36 MB Add to list

Feruloylbenzotriazole and Weinreb amide as bioinspired building blocks: a reactivity study towards O-, N-, S-, and C- nucleophiles

(2014) EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2014(12). p.2594-2611
Author
Organization
Abstract
A versatile route for the conversion of ferulic acid into biologically relevant molecules is presented. The compatibility of a number of protection and activation strategies with the 1,2-addition of a variety of O-, N-, S-, and C-nucleophiles to ferulic acid is evaluated. In particular, this report contains the first systematic study of the addition of (hetero)aryllithium reagents to 3-phenylpropenoyl Weinreb amides. The relevance of this bioinspired method is illustrated by the synthesis of a number of natural products or analogues, such as zingerone, curcuminoids, and (heteroaryl) chalcones.
Keywords
Nucleophilic addition, Nitrogen heterocycles, Biomimetic synthesis, Natural products, KETONES, ACYLATION, ACYLBENZOTRIAZOLES, Lithiation, BIOLOGICAL-ACTIVITIES, EFFICIENT CONVERSION, PRACTICAL SYNTHESIS, FERULIC ACID, CARBOXYLIC-ACIDS, SOFT ENOLIZATION, ACID-DERIVATIVES

Downloads

  • (...).pdf
    • full text
    • |
    • UGent only
    • |
    • PDF
    • |
    • 1.36 MB

Citation

Please use this url to cite or link to this publication:

MLA
Roman, Bart, Jean-Christophe Monbaliu, Laurens De Coen, et al. “Feruloylbenzotriazole and Weinreb Amide as Bioinspired Building Blocks: a Reactivity Study Towards O-, N-, S-, and C- Nucleophiles.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2014.12 (2014): 2594–2611. Print.
APA
Roman, B., Monbaliu, J.-C., De Coen, L., Verhasselt, S., Schuddinck, B., Van Hoeylandt, E., & Stevens, C. (2014). Feruloylbenzotriazole and Weinreb amide as bioinspired building blocks: a reactivity study towards O-, N-, S-, and C- nucleophiles. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014(12), 2594–2611.
Chicago author-date
Roman, Bart, Jean-Christophe Monbaliu, Laurens De Coen, Sigrid Verhasselt, Bart Schuddinck, Evelien Van Hoeylandt, and Christian Stevens. 2014. “Feruloylbenzotriazole and Weinreb Amide as Bioinspired Building Blocks: a Reactivity Study Towards O-, N-, S-, and C- Nucleophiles.” European Journal of Organic Chemistry 2014 (12): 2594–2611.
Chicago author-date (all authors)
Roman, Bart, Jean-Christophe Monbaliu, Laurens De Coen, Sigrid Verhasselt, Bart Schuddinck, Evelien Van Hoeylandt, and Christian Stevens. 2014. “Feruloylbenzotriazole and Weinreb Amide as Bioinspired Building Blocks: a Reactivity Study Towards O-, N-, S-, and C- Nucleophiles.” European Journal of Organic Chemistry 2014 (12): 2594–2611.
Vancouver
1.
Roman B, Monbaliu J-C, De Coen L, Verhasselt S, Schuddinck B, Van Hoeylandt E, et al. Feruloylbenzotriazole and Weinreb amide as bioinspired building blocks: a reactivity study towards O-, N-, S-, and C- nucleophiles. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2014;2014(12):2594–611.
IEEE
[1]
B. Roman et al., “Feruloylbenzotriazole and Weinreb amide as bioinspired building blocks: a reactivity study towards O-, N-, S-, and C- nucleophiles,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2014, no. 12, pp. 2594–2611, 2014.
@article{4411160,
  abstract     = {A versatile route for the conversion of ferulic acid into biologically relevant molecules is presented. The compatibility of a number of protection and activation strategies with the 1,2-addition of a variety of O-, N-, S-, and C-nucleophiles to ferulic acid is evaluated. In particular, this report contains the first systematic study of the addition of (hetero)aryllithium reagents to 3-phenylpropenoyl Weinreb amides. The relevance of this bioinspired method is illustrated by the synthesis of a number of natural products or analogues, such as zingerone, curcuminoids, and (heteroaryl) chalcones.},
  author       = {Roman, Bart and Monbaliu, Jean-Christophe and De Coen, Laurens and Verhasselt, Sigrid and Schuddinck, Bart and Van Hoeylandt, Evelien and Stevens, Christian},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {Nucleophilic addition,Nitrogen heterocycles,Biomimetic synthesis,Natural products,KETONES,ACYLATION,ACYLBENZOTRIAZOLES,Lithiation,BIOLOGICAL-ACTIVITIES,EFFICIENT CONVERSION,PRACTICAL SYNTHESIS,FERULIC ACID,CARBOXYLIC-ACIDS,SOFT ENOLIZATION,ACID-DERIVATIVES},
  language     = {eng},
  number       = {12},
  pages        = {2594--2611},
  title        = {Feruloylbenzotriazole and Weinreb amide as bioinspired building blocks: a reactivity study towards O-, N-, S-, and C- nucleophiles},
  url          = {http://dx.doi.org/10.1002/ejoc.201301895},
  volume       = {2014},
  year         = {2014},
}

Altmetric
View in Altmetric
Web of Science
Times cited: