A pyridinium anionic ring-opening reaction applied to the stereodivergent syntheses of Piperaceae natural products-Reference-Cited by-同舟云学术

A pyridinium anionic ring-opening reaction applied to the stereodivergent syntheses of Piperaceae natural products

Published:2020 Issue:44 Volume:18 Page:9050-9059
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Primdahl Karoline G.¹²³⁴^ORCID,Nolsøe Jens M. J.⁵⁶⁷⁸⁴^ORCID,Aursnes Marius¹²³⁴^ORCID

Affiliation:

1. Department of Pharmaceutical Chemistry

2. University of Oslo

3. 0316 Oslo

4. Norway

5. Faculty of Chemistry

6. Biotechnology and Food Science

7. Norwegian University of Life Sciences

8. 1432 Ås

Abstract

Expanding the scope of a pyridinium ring-opening reaction, a practical oxidation protocol has been devised to access isomerically pure bromodiene esters. The utility is demonstrated in a divergent strategy to obtain two natural TRPV1 agonist motifs.

Funder

Norges Forskningsråd

Universitetet i Oslo

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/OB/D0OB01745K

Reference50 articles.

1. G. M. Strunz , Unsaturated Amides from Piper Species (Piperaceae) , in Studies in Natural Product Chemistry: Bioactive Natural Products , ed. Atta-ur-Rahman , Elsevier Science , 2000 , vol. 24 , pp. 683–738

2. P. N. Ravindran and J. A.Kallupurackal , Black pepper , in Handbook of Herbs and Spices , ed. K. V. Peter , Woodhead Publishing , 2012 , p. 104

3. M. Toussaint-Samat , Spice at Any Price , in History of Food , ed. A. Bell , Translator, Wiley-Blackwell , UK , 2nd edn, 2009 , pp. 441–446

4. Black Pepper and its Pungent Principle-Piperine: A Review of Diverse Physiological Effects

Cited by 4 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Multiply Unsaturated and ω‐Brominated β‐Ketothioesters for Synthesizing β‐Ketolactams and the Scaffolds of Fully Enolized N‐Hydroxy‐3‐(polyenoyl)pyridine‐2,4‐dione Natural Products;European Journal of Organic Chemistry;2023-12-22

2. Anti-inflammatory activity and cytotoxicity against ovarian cancer cell lines by amide alkaloids and piperic esters isolated from Piper longum fruits: In vitro assessments and molecular docking simulation;Bioorganic Chemistry;2022-11

3. On the Structure of Thailandene A: Synthetic Examination of the Cryptic Natural Product Aided by a Theoretical Approach;Synthesis;2022-01-17

4. Insight into the Modes of Activation of Pyridinium and Bipyridinium Salts in Non‐Covalent Organocatalysis;Advanced Synthesis & Catalysis;2021-09-03