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


  • Financial support from The Netherlands Organization for Scientific Research (NWO-CW) is acknowledged. S. B. thanks the Generalitat Valenciana and the Universitat de València (Spain) for a postoctoral grant (VALi+D program).


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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.