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Diastereoselective Synthesis of Cyclopentanoids: Applications to the Construction of the ABCD Tetracyclic Core of Retigeranic Acid A
Author(s) -
Zhang Junlin,
Wang Xiao,
Li Shuang,
Li Dian,
Liu Song,
Lan Yu,
Gong Jianxian,
Yang Zhen
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502423
Subject(s) - stereocenter , intramolecular force , stereochemistry , chemistry , quaternary carbon , core (optical fiber) , carbon skeleton , cycloaddition , combinatorial chemistry , catalysis , enantioselective synthesis , organic chemistry , computer science , telecommunications
A concise and efficient approach for the construction of the tetracyclic carbon skeleton of retigeranic acid A is described. The key transformations include a novel Rh‐catalyzed [3+2] cycloaddition of enyol to afford cyclopentanoid E , bearing two contiguous quaternary stereocenters at the bridgehead positions, and an intramolecular Pauson–Khand reaction to construct the advanced tetracyclic core structure of retigeranic acid A.