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

Article abstract of DOI:10.1016/S0040-4020(96)00950-7

An expeditious total synthesis of the physiologically active fungal metabolite 1 is described, The stereoselective formation of its β-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 β-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.