Premium
Total Synthesis of Vinigrol
Author(s) -
Yang Qingliang,
Njardarson Jon T.,
Draghici Cristian,
Li Fang
Publication year - 2013
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.201304624
Subject(s) - stereocenter , total synthesis , cycloaddition , chemistry , fragmentation (computing) , stereochemistry , ring (chemistry) , catalysis , substrate (aquarium) , combinatorial chemistry , organic chemistry , enantioselective synthesis , computer science , biology , ecology , operating system
Carbocyclic cage fight : The substrate‐controlled total synthesis of vinigrol features a strategic oxidative dearomatization/Diels–Alder cycloaddition reaction and a subsequent palladium‐catalyzed cyclization cascade to construct the carbocyclic core. The C4, C9, and C12 stereocenters were installed using either reduction or oxidation reactions, and the diterpenoid core was unraveled by a ring fragmentation reaction.