| Autor: |
Barroso, Santiago, Geerdink, Danny, ter Horst, Bjorn, Casas-Arce, Eva, Minnaard, Adriaan J. |
| Přispěvatelé: |
Stratingh Institute of Chemistry, Chemical Biology 2, Synthetic Organic Chemistry |
| Jazyk: |
angličtina |
| Rok vydání: |
2013 |
| Předmět: |
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| Zdroj: |
European Journal of Organic Chemistry, 2013(21), 4642-4654. WILEY-V C H VERLAG GMBH |
| ISSN: |
1434-193X |
| Popis: |
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 -keto ester afforded the basis for the central 1,3-diol moiety, and introduction of the 2-O-methyl--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. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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