Enantioselective synthesis of the papulacandin ring system: Conversion of the mannose diastereoisomer into a glucose stereoisomer

Organic Letters

Volumn 2, Issue 25, 2000, Pages 4033-4036

  Balachari, Devan ^a   O'Doherty, George A ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOGLYCOSIDE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; GLUCOSE; MANNOSE; PAPULACANDINS;

ARTICLE; CHEMISTRY; HYDROXYLATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTIFUNGAL; GLUCOSE; HYDROXYLATION; MANNOSE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 0034649738     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006662a     Document Type: Article

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46. The significance of this procedure is evident in that previous synthetic routes to the glucose paplulacandin isomer 1 only provided impure materials, which were characterized as their tetraacetates: see ref 12i.
47. The allose papulacandin 3 was also prepared from 8 by this sequence; however, the intermediate triol was difficult to characterize because of TBS group migration.