Concise Synthesis of Broussonone A

Molecules

Hyeju Jo³  Minho Choi³  Mayavan Viji³  Young Hee Lee³  Young-Shin Kwak²  Kiho Lee²  Nam Song Choi¹  Yeon-Ju Lee⁴  Heesoon Lee³  Jin Tae Hong³  Mi Kyeong Lee³  Jae-Kyung Jung³ 

[1] College of Interdisciplinary & Creative Studies, Konyang University, Nonsan 320-711, Korea; E-Mail:;College of Pharmacy, Korea University, Sejong 339-700, Korea; E-Mail:;College of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 362-763, Korea; E-Mails:;Korea Ocean Research and Development Institute, Ansan 426-44, Korea; E-Mail:

关键词: broussonone A;    cross metathesis;    Grubbs catalyst;    oxidative dearomatization;    PIFA;    total synthesis;   

DOI  :  10.3390/molecules200915966

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.