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Inside Back Cover: Diastereoselective Synthesis of Cyclopentanoids: Applications to the Construction of the ABCD Tetracyclic Core of Retigeranic Acid A (Chem. Eur. J. 36/2015)
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 - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201583603
Subject(s) - stereocenter , intramolecular force , stereochemistry , chemistry , quaternary carbon , ring (chemistry) , carbon skeleton , total synthesis , core (optical fiber) , combinatorial chemistry , catalysis , enantioselective synthesis , organic chemistry , computer science , telecommunications
Tetracyclic carbon skeleton construction: Retigeranic acids are challenging synthetic targets owing to their pentacyclic skeletons that feature an unusual trans ‐hydrindane ring system, a cyclopentanoid with two quaternary carbon centers at its bridgehead positions, and eight stereogenic centers of which three are quaternary. In their Communication of page 12596 ff. , Y. Lan, J. Gong, Z. Yang and co‐workers report a concise and efficient construction of the tetracyclic carbon skeleton of retigeranic acid A. Key transformations include a Rh‐catalyzed [3+2] cycloaddition of enyol to give the two contiguous quaternary stereocenters at the cyclopentanoid bridgehead positions, and an intramolecular Pauson–Khand reaction to construct the tetracyclic core.