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

被引:77
作者
Furstner, A
Konetzki, I
机构
[1] Max-Planck-Inst. fur Kohlenforschung, D-45470 Mülheim/Ruhr
关键词
D O I
10.1016/S0040-4020(96)00950-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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
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页码:15071 / 15078
页数:8
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