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Collective Synthesis of Cladiellins Based on the Gold‐Catalyzed Cascade Reaction of 1,7‐Diynes
Author(s) -
Yue Guozong,
Zhang Yun,
Fang Lichao,
Li Chuangchuang,
Luo Tuoping,
Yang Zhen
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201309449
Subject(s) - cascade reaction , combinatorial chemistry , chemistry , tandem , catalysis , cascade , ring (chemistry) , modular design , bicyclic molecule , molecule , stereochemistry , organic chemistry , computer science , materials science , chromatography , composite material , operating system
The cladiellin family of natural products, which includes molecules with various biological activities, continues to invite new synthetic studies. A gold‐catalyzed tandem reaction of 1,7‐diynes to construct the 6‐5‐bicyclic ring systems that are present in a number of natural products was developed. This reaction was applied as the key step to realize the formal and total syntheses of nine members of the cladiellin family in an enantio‐ and diastereoselective manner. This modular and efficient approach could also be used for the construction of other cladiellins, as well as their analogues, for follow‐up studies.