P-44 トコフェロール基本骨格の光学活性クロマンエタノールの酵素触媒合成(ポスター発表の部)

抄録

Recently, many tocopherol analogs have been examined as antioxidants to find several effective hydrophilic scavengers of super oxide series such as trolox and MDL-73404. Particularly, MDL-73404 has cardioprotective properties and is under development for the reduction of myocardial infarct size. We now wish to report the asymmetric synthesis of (S)-MDL-73404 by lipase-catalyzed resolution of racemic chromanethanol, which could be led to the other tocopherol analogs. The transesterification of vinyl acetate by using lipaseB (Pseudomonas sp.) gave enantiomerically pure (>99%ee) (S)-chromanethanol, that was then converted to (S)-(-)-MDL-73404. The (R)-chromanethanol as by-product of lipase-catalyzed resolution was inverted to the (S)-isomer in four steps.