Premium
Synthesis of the Kedarcidin Core Structure by a Transannular Cyclization Pathway
Author(s) -
Myers Andrew G.,
Goldberg Steven D.
Publication year - 2000
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 - 10.1002/1521-3773(20000804)39:15<2732::aid-anie2732>3.0.co;2-9
Subject(s) - enediyne , chromophore , enantioselective synthesis , chemistry , bromide , stereochemistry , lithium (medication) , combinatorial chemistry , halogen , core (optical fiber) , organic chemistry , materials science , catalysis , medicine , alkyl , endocrinology , composite material
The chromoprotein enediyne antibiotic kedarcidin has a structurally complex and highly reactive chromophore component. An enantioselective synthesis of compound 1 , which contains the full functionality of the chromophore core, is described. The key step in the synthetic route involves low‐temperature halogen–lithium exchange initiated transannular cyclization of the macrocyclic vinyl bromide 2 . TBS= tert ‐butyldimethylsilyl.