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. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Total synthesis of the triglycosyl phenolic glycolipid PGL-tb1 from mycobacterium tuberculosis / Barroso, Santiago; Castelli, Riccardo; Baggelaar, Marc P.; Geerdink, Danny; Terhorst, Bjorn; Casas Arce, Eva; Overkleeft, Herman S.; Van Der Marel, Gijsbert A.; Codée, Jeroen D. C.; Minnaard, Adriaan J.. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - 51:47(2012), pp. 11774-11777. [10.1002/anie.201206221]

Total synthesis of the triglycosyl phenolic glycolipid PGL-tb1 from mycobacterium tuberculosis

CASTELLI, Riccardo;
2012-01-01

Abstract

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. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
2012
Total synthesis of the triglycosyl phenolic glycolipid PGL-tb1 from mycobacterium tuberculosis / Barroso, Santiago; Castelli, Riccardo; Baggelaar, Marc P.; Geerdink, Danny; Terhorst, Bjorn; Casas Arce, Eva; Overkleeft, Herman S.; Van Der Marel, Gijsbert A.; Codée, Jeroen D. C.; Minnaard, Adriaan J.. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - 51:47(2012), pp. 11774-11777. [10.1002/anie.201206221]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2815688
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