Biomimetic Epoxide-Opening Cascades of Oxasqualenoids Triggered by Hydrolysis of the Terminal Epoxide

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• 作者：Yoshiki Morimoto ; Eriko Takeuchi ; Hitomi Kambara ; Takeshi Kodama ; Yoshimitsu Tachi ; Keisuke Nishikawa
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：June 21, 2013
• 年：2013
• 卷：15
• 期：12
• 页码：2966-2969
• 全文大小：329K
• 年卷期：v.15,no.12(June 21, 2013)
• ISSN：1523-7052

文摘

The biomimetic epoxide-opening cascades from squalene polyepoxides 4鈥?b>6 to triterpene polyethers (oxasqualenoids) teurilene (1), glabrescol (2), and omaezakianol (3), respectively, were reproduced in a single event by chemical reaction. These cascades proceeded through the 5-exo tandem cyclization triggered by Br酶nsted acid-catalyzed hydrolysis of the terminal epoxide, mimicking the direct hydrolysis mechanism of epoxide hydrolases.