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Total Synthesis of the Phenolic Glycolipid Mycoside B and the Glycosylated p ‐Hydroxybenzoic Acid Methyl Ester HBAD‐I, Virulence Markers of Mycobacterium tuberculosis
Author(s) -
Barroso Santiago,
Geerdink Danny,
ter Horst Bjorn,
CasasArce Eva,
Minnaard Adriaan J.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300437
Subject(s) - chemistry , moiety , mycobacterium tuberculosis , glycolipid , glycosylation , stereochemistry , total synthesis , stereoselectivity , sonogashira coupling , mycobacterium bovis , mycobacterium , catalysis , biochemistry , bacteria , tuberculosis , palladium , medicine , pathology , biology , genetics
The phenolic glycolipid mycoside B, present in Mycobacterium bovis and hypervirulent strains of Mycobacterium tuberculosis , has been synthesized for the first time. Multiple methyl groups were introduced by the extensive use of catalytic asymmetric 1,4‐addition reactions, asymmetric hydrogenation of a β‐keto ester afforded the basis for the central 1,3‐diol moiety, and introduction of the 2‐ O ‐methyl‐α‐ L ‐rhamnoside unit was achieved by stereoselective glycosylation with p ‐iodophenol and subsequent Sonogashira coupling, providing a basis for the generation of analogues. In addition, the related monosaccharide HBAD‐I, present in the same species, has been efficiently synthesized for the first time by selective methylation of the hydroxy group at C‐2 of a rhamnoside.