Cephalodiones A-D: Compound Characterization and Semisynthesis by [6+6] Cycloaddition
Cephalodiones A-D: Compound Characterization and Semisynthesis by [6+6] Cycloaddition
复制标题
头孢二酮 A–D：通过 [6 6] 环加成进行化合物表征和半合成
DOI：
10.1002/anie.202015332
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发表时间：
2021-03-10
影响因子：
16.6
通讯作者：
Yue, Jian-Min
中科院分区：
文献类型：
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作者：
Ge, Zhan-Peng;Fan, Yao-Yue;Yue, Jian-Min
Cephalodiones A-D (1-4) 是 C-19-降二萜二聚体的第一个例子，是从三尖杉属植物中分离出来并进行充分表征的。这些新的骨架天然产物具有独特的三环[6.4.1.1(2,7)]tetradeca-3,5,9,11-四烯-13,14-二酮核心，其两端均被刚性多环系统C-2-对称或不对称封端。化合物 1-4 被认为是通过两个相同的 C-19-降二萜类姜黄素的 [6+6]-环加成生物合成产生的，这通过二聚体 2-4 的半合成得到了验证。此外，一些化合物对 Th17 细胞分化表现出显着的抑制作用。
Cephalodiones A-D (1-4), the first example of C-19-norditerpenoid dimers, were isolated and fully characterized from a Cephalotaxus plant. These new skeletal natural products shared a unique tricyclo[6.4.1.1(2,7)]tetradeca-3,5,9,11-tetraene-13,14-dione core that was capped in both ends with rigid multicyclic ring systems either C-2-symmetrically or asymmetrically. Compounds 1-4 were proposed to be biosynthetically produced by the [6+6]-cycloaddition of two identical C-19-norditerpenoid troponoids, which was validated by the semisyntheses of dimers 2-4. Moreover, some compounds showed significant inhibition on Th17 cell differentiation.