Synthesis of the branched C-glycoside substructure of altromycin B.
Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b). [reaction: see text]
Koo
Bonsuk
B
Department of Chemistry, Emory University, Atlanta, GA 30322, USA.
McDonald
Frank E
FE
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism; D014414:Tungsten / Q000737:chemistry
D000617:Aminoglycosides; C063717:altromycin B; D014414:Tungsten