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Total Synthesis and Structural Revision of Antibiotic CJ‐16,264
Author(s) -
Nicolaou K. C.,
Shah Akshay A.,
Korman Henry,
Khan Tabrez,
Shi Lei,
Worawalai Wisuttaya,
Theodorakis Emmanuel A.
Publication year - 2015
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.201504337
Subject(s) - decalin , citronellal , total synthesis , stereochemistry , antibiotics , chemistry , molecule , combinatorial chemistry , organic chemistry , catalysis , biochemistry
The total synthesis and structural revision of antibiotic CJ‐16,264 is described. Starting with citronellal, the quest for the target molecule featured a novel bis‐transannular Diels–Alder reaction that casted stereoselectively the decalin system and included the synthesis of six isomers before demystification of its true structure.