Stereochemical course of 5-lipoxygenation of arachidonate by rat basophil leukemic cell (RBL-1) and potato enzymes
Stereochemical course of 5-lipoxygenation of arachidonate by rat basophil leukemic cell (RBL-1) and potato enzymes
复制标题
大鼠嗜碱性粒细胞白血病细胞（RBL-1）和马铃薯酶对花生四烯酸进行 5-脂氧合的立体化学过程
DOI：
10.1021/ja00350a059
复制
发表时间：
1983
影响因子：
15
通讯作者：
P. Lansbury
中科院分区：
文献类型：
--
作者：
E. Corey;P. Lansbury
13 14 16转化为相应的α，β-不饱和醛（1.42当量的四乙酸铅，[13]= 0.2 M，在二氯甲烷中，1.5 hat-65 C），使其与叶立德14* 11反应（1：1 THF-甲苯，-78 ℃），脱保护（1.25mM盐酸在3：1 THF-水中，22 ℃下1小时）后，得到二烯醇15（30%，来自13）。如上文对9所述，将二烯醇15以82%的产率转化为鏻盐12。通过醛16712与由12的去质子化衍生的叶立德（0.87当量的六甲基二硅氮钠，甲苯，0 ℃）的Wittig偶联10组装4的完整碳骨架，经色谱得到4甲酯。从质谱分析确定氘在4甲基酯中的掺入为93.7%。13 - 4甲酯在氩气保护下冻存于苯中，水解
13 14 16 to the corresponding ß,-unsaturated aldehyde (1.42 equiv of lead tetraacetate,[13]= 0.2 M in methylene chloride for 1.5 hat-65 C), which was allowed to react with ylide 14* 11 (1: 1 THF-toluene at-78 C) to afford, after deprotection (1.25 mM hydrochloric acid in 3: 1 THF-water, 1 h at 22 C), dienol 15 (30% from 13). Dienol 15 was converted to phosphonium salt 12 in 82% yield as described above for 9. The complete carbon skeleton of 4 was assembled by Wittig coupling10 of aldehyde 16712 with the ylide derived from deprotonation of 12 (0.87 equiv of sodium hexa-methyldisilazide, toluene, 0 C) to afford after chromatography 4 methyl ester. Deuterium incorporation in 4 methyl ester was determined to be 93.7% from mass spectral analysis. 13 4 methyl ester was stored in frozen benzene under argon and hydrolyzed