One-Step Semisynthesis of a Segetane Diterpenoid from a Jatrophane Precursor via a Diels–Alder Reaction

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• 作者：Luo-Sheng Wan ; Li-Dong Shao ; Liangbing Fu ; Jun Xu ; Guo-Lei Zhu ; Xing-Rong Peng ; Xiao-Nian Li ; Yan Li ; Ming-Hua Qiu
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：18
• 期：3
• 页码：496-499
• 全文大小：271K
• ISSN：1523-7052

文摘

A novel segetane diterpenoid (1) and four jatrophane diterpenoids (2–5) were isolated from an acetone extract of Euphorbia peplus. Due to quantity limitations, we prepared 1 via a Diels–Alder reaction, an approach motivated by this compound’s biosynthetic pathway and successfully performed X-ray analysis of 1. Furthermore, in an in vitro activity test, 1 exhibited moderate anti-inflammatory activity, whereas both its precursor (2) and the relevant intermediate (2a, IC₅₀ = 1.56 μM) exhibited significant anti-inflammatory activity.