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Total Syntheses of Crinipellins Enabled by Cobalt‐Mediated and Palladium‐Catalyzed Intramolecular Pauson–Khand Reactions
Author(s) -
Huang Zhihui,
Huang Jun,
Qu Yongzheng,
Zhang Weibin,
Gong Jianxian,
Yang Zhen
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201805143
Subject(s) - palladium , pauson–khand reaction , intramolecular force , cobalt , catalysis , chemistry , combinatorial chemistry , stereochemistry , organic chemistry
Efficient total syntheses of the naturally occurring, potent antibiotic compounds (−)‐crinipellin A and (−)‐crinipellin B are described. The key advanced intermediate, a fully functionalized tetraquinane core, was constructed by a novel thiourea/palladium‐catalyzed Pauson–Khand reaction. This intermediate can serve as a common intermediate for the collective total synthesis of other members of the crinipellin family.