Biomimetic Synthesis of Zeylanone and Zeylanone Epoxide by Dimerization of 2-Methyl-1,4-naphthoquinone

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• 作者：Sayako Maruo ; Kazuyuki Nishio ; Takahiro Sasamori ; Norihiro Tokitoh ; Kouji Kuramochi ; Kazunori Tsubaki
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：April 5, 2013
• 年：2013
• 卷：15
• 期：7
• 页码：1556-1559
• 全文大小：280K
• 年卷期：v.15,no.7(April 5, 2013)
• ISSN：1523-7052

文摘

A biomimetic synthesis of zeylanone and zeylanone epoxide, which are natural dimeric naphthoquinones, has been accomplished starting from plumbagin, a natural monomeric naphthoquinone. The key features of our synthesis are cascade intermolecular and intramolecular Michael reactions, followed by epoxidation of the resultant hydroquinone with molecular oxygen.