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Journal Article

Synthesis of 2-Hydroxy-6-{[(16R)-ß-D-mannopyranosyloxy]heptadecyl}benzoic Acid, a Fungal Metabolite with GABAA Ion Channel Receptor Inhibiting Properties

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Konetzki,  Ingo
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., & Konetzki, I. (1996). Synthesis of 2-Hydroxy-6-{[(16R)-ß-D-mannopyranosyloxy]heptadecyl}benzoic Acid, a Fungal Metabolite with GABAA Ion Channel Receptor Inhibiting Properties. Tetrahedron, 52(48), 15071-15078. doi:10.1016/S0040-4020(96)00950-7.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-1DB0-9
Abstract
An expeditious total synthesis of the physiologically active fungal metabolite 1 is described. The stereoselective formation of its ß-D-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 ß-D-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.