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Cephalodiones A–D: Compound Characterization and Semisynthesis by [6+6] Cycloaddition
Author(s) -
Ge ZhanPeng,
Fan YaoYue,
Deng WenDe,
Zheng ChengYu,
Li Ting,
Yue JianMin
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202015332
Subject(s) - semisynthesis , cycloaddition , chemistry , stereochemistry , diterpene , ring (chemistry) , organic chemistry , catalysis
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.