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Semisynthesis of 3‐Hydroxyoxindole Rapamycin Analogues Through Site‐ and Stereoselective Trapping of Oxonium Ylides in Rh II ‐Catalyzed Three‐Component Reactions
Author(s) -
Qiu Lin,
Su Meng,
Wen Zhongqing,
Zhu Xiangcheng,
Duan Yanwen,
Huang Yong
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900338
Subject(s) - oxonium ion , chemistry , semisynthesis , ylide , stereoselectivity , catalysis , surface modification , stereochemistry , trapping , combinatorial chemistry , organic chemistry , ion , ecology , biology
The site‐ and diastereoselective functionalization of 40‐OH in rapamycin by 3‐hydroxyoxindole moieties was efficiently achieved through the active protic oxonium ylide trapping reactions using isatins, resulting in 31 new analogues of rapamycin. This study not only significantly expanded the known active rapalogs, but showcased the broad utility of multi‐component reactions in late‐stage functionalization of complex natural products.