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Concise Synthesis of Broussonone A.

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.

SUBMITTER: Jo H

PROVIDER: S-EPMC6331890 | biostudies-other | 2015 Sep

REPOSITORIES: biostudies-other

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Concise Synthesis of Broussonone A.

Jo Hyeju H Choi Minho M Viji Mayavan M Lee Young Hee YH Kwak Young-Shin YS Lee Kiho K Choi Nam Song NS Lee Yeon-Ju YJ Lee Heesoon H Hong Jin Tae JT Lee Mi Kyeong MK Jung Jae-Kyung JK

Molecules (Basel, Switzerland) 20150902 9

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 u ...[more]

PMID: 26364628

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