Synthesis of 2-hydroxy-6-{[(16 R)-β-δ-mannopyransyloxy]heptadecyl}benzoic acid, a fungal metabolite with GABA A ion channel receptor inhibiting properties

An expeditious total synthesis of the physiologically active fungal metabolite 1 is described. The stereoselective formation of its β-δ-mannopyranosidic linkage is achieved in two steps upon reaction of the hexopyranos-2-ulosyl bromide 15 with the glycosyl acceptor 13, followed by reduction of the r...

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Bibliographic Details
Published inTetrahedron Vol. 52; no. 48; pp. 15071 - 15078
Main Authors Fürstner, Alois, Konetzki, Ingo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.11.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANOBORON COMPOUNDS
GLYCOSIDES
HALIDES
BETA-MANNOPYRANOSIDES
CROSS-COUPLING REACTIONS
ANTIBIOTICS
PRACTICAL SYNTHESIS
OLIGOSACCHARIDES
MANNOSE
INTRAMOLECULAR AGLYCON DELIVERY
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Summary:An expeditious total synthesis of the physiologically active fungal metabolite 1 is described. The stereoselective formation of its β-δ-mannopyranosidic linkage is achieved in two steps upon reaction of the hexopyranos-2-ulosyl bromide 15 with the glycosyl acceptor 13, followed by reduction of the resulting β-δ-glycos-2-uloside 16. Alcohol 13 was efficiently prepared via a Suzuki reaction of the aryltriflate 11 with the 9-alkyl-9-BBN derivative 10. A stereoselective synthesis of the physiologically active β-D-mannopyranoside 1 is described.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(96)00950-7