Synthesis of 2-Hydroxy-6-{[(16R)-beta-D-mannopyranosyloxy]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 beta-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 beta-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. Copyright (C) 1996 Elsevier Science Ltd