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Rhodium(III)‐Catalyzed Intramolecular Annulation through CH Activation: Total Synthesis of (±)‐Antofine, (±)‐Septicine, (±)‐Tylophorine, and Rosettacin
Author(s) -
Xu Xianxiu,
Liu Yu,
Park CheolMin
Publication year - 2012
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.201204970
Subject(s) - annulation , intramolecular force , chemistry , regioselectivity , rhodium , catalysis , alkyne , functional group , total synthesis , substrate (aquarium) , stereochemistry , combinatorial chemistry , medicinal chemistry , scope (computer science) , organic chemistry , computer science , oceanography , programming language , geology , polymer
Annulation : The efficient synthesis of 3‐hydroxyalkyl isoquinolones and 6‐hydroxyalkyl 2‐pyridones is enabled through the intramolecular annulation of alkyne‐tethered hydroxamic esters (see scheme, Cp*=pentamethylcyclopentadienyl). The reaction features high regioselectivity, broad substrate scope, and excellent functional‐group tolerance, proceeds under mild reaction conditions with low catalyst loading, and obviates the need for an external oxidant.