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Total Synthesis of the Triglycosyl Phenolic Glycolipid PGL-tb1 from Mycobacterium tuberculosis

By Santiago Barroso, Riccardo Castelli, Marc P. Baggelaar, Danny Geerdink, Bjorn ter Horst, Eva Casas-Arce, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D.C. Codée and Adriaan J. Minnaard


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.

Year: 2012
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