Racemic and optically active 2-methoxy-4-oxatetradecanoic acids: novel synthetic fatty acids with selective antifungal properties
作者:Néstor M. Carballeira、Rosann O’Neill、Keykavous Parang
DOI:10.1016/j.chemphyslip.2005.03.002
日期:2005.7
The unprecedented (+/-)-2-methoxy-4-oxatetradecanoic acid and the optically pure (S)-2-methoxy-4-oxatetradecanoic acid were synthesized in six steps and in 11-14% overall yields starting with either 1,2-O-isopropylidene-rac-glycerol or 1,2-O-isopropylidene-(S)-glycerol. The key step in the synthesis was the selective monosilylation of a dibutylstannylene intermediate. The title compounds displayed
前所未有的(+/-)-2-甲氧基-4-草酸酯双磺酸和光学纯的(S)-2-甲氧基-4-草酸酯双硬脂酸是通过六个步骤合成的,总收率为11-14%,从任一方法开始, 2-O-异亚丙基-rac-甘油或1,2-O-异亚丙基-(S)-甘油。合成中的关键步骤是二丁基亚锡中间体的选择性单硅烷化。标题化合物对新型隐球菌ATCC 66031和黑曲霉ATCC 16404表现出0.08-0.22 mM的选择性真菌毒性,但对白色念珠菌ATCC 14053和ATCC 60193没有显着活性(> 2.6 mM)。尽管是N-肉豆蔻酰基转移酶(NMT)的良好底物,但氧化的2-甲氧基化化合物的外消旋物和S-对映异构体在抗真菌活性方面没有显着差异。