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Molecules 2015, 20(9), 15966-15975; doi:10.3390/molecules200915966

Concise Synthesis of Broussonone A

1
College of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 362-763, Korea
2
College of Pharmacy, Korea University, Sejong 339-700, Korea
3
College of Interdisciplinary & Creative Studies, Konyang University, Nonsan 320-711, Korea
4
Korea Ocean Research and Development Institute, Ansan 426-44, Korea
*
Authors to whom correspondence should be addressed.
Academic Editor: Joshua G. Pierce
Received: 3 August 2015 / Revised: 22 August 2015 / Accepted: 25 August 2015 / Published: 2 September 2015
(This article belongs to the Special Issue Natural Product Synthesis: A Platform for Discovery)
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Abstract

A concise and expeditious approach to the total synthesis of broussonone A, a p-quinol natural compound, has been developed. The key features of the synthesis include the Grubbs II catalyst mediated cross metathesis of two aromatic subunits, and a chemoselective oxidative dearomatizationin the presence of two phenol moieties. Especially, optimization associated with the CM reaction of ortho-alkoxystyrenes was also studied, which are known to be ineffective for Ru-catalyzed metathesis reactions under conventional reaction conditions because ortho-alkoxy group could coordinate to the ruthenium center, resulting in the potential complication of catalyst inhibition. View Full-Text
Keywords: broussonone A; cross metathesis; Grubbs catalyst; oxidative dearomatization; PIFA; total synthesis broussonone A; cross metathesis; Grubbs catalyst; oxidative dearomatization; PIFA; total synthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Jo, H.; Choi, M.; Viji, M.; Lee, Y.H.; Kwak, Y.-S.; Lee, K.; Choi, N.S.; Lee, Y.-J.; Lee, H.; Hong, J.T.; Lee, M.K.; Jung, J.-K. Concise Synthesis of Broussonone A. Molecules 2015, 20, 15966-15975.

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