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Total Synthesis of the Triglycosyl Phenolic Glycolipid PGL‐tb1 from Mycobacterium tuberculosis
Author(s) -
Barroso Santiago,
Castelli Riccardo,
Baggelaar Marc P.,
Geerdink Danny,
ter Horst Bjorn,
CasasArce Eva,
Overkleeft Herman S.,
van der Marel Gijsbert A.,
Codée Jeroen D. C.,
Minnaard Adriaan J.
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.201206221
Subject(s) - glycolipid , sonogashira coupling , mycobacterium tuberculosis , chemistry , mycobacterium , trisaccharide , microbiology and biotechnology , stereochemistry , bacteria , tuberculosis , biochemistry , biology , catalysis , medicine , palladium , genetics , pathology
Complex : The synthesis of the glycolipid PGL‐tb1 present in the outer membrane of hypervirulent strains of Mycobacterium tuberculosis has been accomplished for the first time by using a highly convergent strategy featuring a Sonogashira coupling to unite a phenolic trisaccharide with the phthiocerol. Efficient asymmetric Cu‐catalyzed 1,4‐additions to unsaturated thioesters and cyclic enones have been employed to introduce the methyl groups.