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

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posted on 04.02.2016, 16:06 by Luo-Sheng Wan, Li-Dong Shao, Liangbing Fu, Jun Xu, Guo-Lei Zhu, Xing-Rong Peng, Xiao-Nian Li, Yan Li, Ming-Hua Qiu
A novel segetane diterpenoid (1) and four jatrophane diterpenoids (25) 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.