Stereoselective synthesis of vancosamine and saccharosamine glycals via tungsten-catalyzed alkynol cycloisomerization

Organic Letters

Volumn 4, Issue 5, 2002, Pages 749-752

  Cutchins, William W ^a   McDonald, Frank E ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AMINOSUGAR; ANTIINFECTIVE AGENT; DEOXYSUGAR; HEXOSAMINE; SUCROSE; TUNGSTEN; VANCOSAMINE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKYNES; AMINO SUGARS; ANTI-BACTERIAL AGENTS; CATALYSIS; CYCLIZATION; DEOXY SUGARS; HEXOSAMINES; STEREOISOMERISM; SUCROSE; TUNGSTEN;

EID: 0037035003     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017195f     Document Type: Article

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28. 3N or DABCO, THF, hv = 350 nm), we could not raise the yield of the reaction above ca. 30%, nor could we separate the glycal from the many other unidentified byproducts. We suspect that the p-methoxyphenylamine is poorly compatible with the reaction, either from complexation of the amine with the tungsten catalyst or photolytic degradation of the electron-rich aromatic system.