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A Suzuki-Miyaura Coupling of ortho-Hydroxyaryl Bromide with Isopropenylboronic Pinacol Ester: Synthesis of the Potassium-Channel Opener (+)-Callitrisic Acid
Linköping University, Department of Physics, Chemistry and Biology, Chemistry. Linköping University, Faculty of Science & Engineering.
Linköping University, Department of Clinical and Experimental Medicine, Divison of Neurobiology. Linköping University, Faculty of Medicine and Health Sciences.
Linköping University, Department of Clinical and Experimental Medicine, Divison of Neurobiology. Linköping University, Faculty of Medicine and Health Sciences.
Linköping University, Department of Clinical and Experimental Medicine, Divison of Neurobiology. Linköping University, Faculty of Medicine and Health Sciences.ORCID iD: 0000-0001-9125-5583
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2018 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 14, p. 1730-1734Article in journal (Refereed) Published
Abstract [en]

A Suzuki-Miyaura coupling reaction of ortho-hydroxy-aromatic bromide 8 with isopropenylboronic acid pinacol ester has been investigated. It was found that the catalyst of Pd-2(dba)(3)/PCy3 in dioxan-water gave good yield by suppressing the formation of isomeric side product 14. (+)-Callitrisic acid was synthesized from (+)-podocarpic acid using this condition with an overall yield of 54 % in about five steps. (+)-Callitrisic acid was found to be almost three times more potent than dehydroabietic acid to open a voltage-gated potassium channel.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2018. no 14, p. 1730-1734
Keywords [en]
Suzuki-Miyaura; (+)-Callitrisic acid; Potassium ion channels; Cross-coupling; Podocarpic acid
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:liu:diva-147800DOI: 10.1002/ejoc.201800070ISI: 000430286900014OAI: oai:DiVA.org:liu-147800DiVA, id: diva2:1205639
Note

Funding Agencies|Center for Systems Neurobiology, Linkopings Univetsitet; Swedish Research Council; Swedish Brain Foundation; Swedish Heart-Lung Foundation

Available from: 2018-05-14 Created: 2018-05-14 Last updated: 2018-05-14

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Wu, XiongyuSilverå Ejneby, MalinOttosson, NinaElinder, FredrikKonradsson, Peter
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European Journal of Organic Chemistry
Organic Chemistry

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