Novel Entry into 5-Decarboxydibenzofurans via Smiles Rearrangement of the Lichen Para-Depside, Erythrin-Reference-Cited by-同舟云学术

Novel Entry into 5-Decarboxydibenzofurans via Smiles Rearrangement of the Lichen Para-Depside, Erythrin

Published:2010-03 Issue:3 Volume:34 Page:154-157
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Thadhani Vinitha M.¹,Choudhary Muhammad Iqbal²,Andersen Raymond J.³,Karunaratne Veranja¹

Affiliation:

1. Department of Chemistry, University of Peradeniya, Peradeniya, Sri Lanka

2. H.E.J. Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan

3. Departments of Chemistry & Earth and Ocean Sciences, University of British Columbia, Vancouver, B.C., Canada V6T 1Z1

Abstract

Erythrin, isolated in 7.3% yield from the lichen Roccella montagnei, was converted via a Smiles rearrangement to a series of diphenyl ethers. Those with a free carboxylic acid at C-1 underwent a novel decarboxylative oxidative cyclisation in the presence of Pd(OAc)2 to produce 5-decarboxydibenzofurans. All compounds were assayed for their antioxidant and β-glucuronidase enzyme inhibitory activity.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/030823410X12677394014276

Reference20 articles.

1. HawksworthD.L., KirkP. M., SuttonB. C., and PeglerD. N., Ainsworth and Bisbys; dictionary of the fungi, CAB International, Wallingford, 1995, Vol. 8, pp 616.

2. RomagniJ.G., RosellR. C., NanayakkaraN. P. D., and DayanF. E., Ecophysiology and potential modes of action for selected lichen secondary metabolites; allelopathy CRC Press, Boca, Raton. 2004, pp. 13.

3. Identification of Lichen Substances

4. A Novel Synthesis of the Lichen Depsidones Divaronic Acid and Stenosporonic Acid, and the Biosynthetic Implications

Cited by 10 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. Synthesis of novel bis-thiazoles, bis-thienopyridines, and bis-triazolothiadiazines linked to diphenyl ether core as novel hybrid molecules;Synthetic Communications;2023-02-17

2. Chemical diversities, biological activities and chemical synthesis of marine diphenyl ether and their derivatives;Journal of Molecular Structure;2022-10

3. Diphenyl Ethers from a Marine-Derived Aspergillus sydowii;Marine Drugs;2018-11-16

4. Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis;Angewandte Chemie International Edition;2017-09-26

5. Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis;Angewandte Chemie;2017-09-26