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Dr. Santiago Barroso, Dr. Riccardo Castelli, Marc P. Baggelaar, Danny Geerdink, Dr. Bjorn ter Horst, Dr. Eva Casas-Arce, Prof. Herman S. Overkleeft, Prof. Gijsbert A. van der Marel, Dr. Jeroen D. C. Codée and Prof. Adriaan J. Minnaard Total Synthesis of the Triglycosyl Phenolic Glycolipid PGL-tb1 from Mycobacterium tuberculosis Angewandte Chemie International Edition 51

Version of Record online: 19 OCT 2012 | DOI: 10.1002/anie.201206221

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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.

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