Asymmetric synthesis of four diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid: proof of configurational assignment.
Asymmetric synthesis of four diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid: proof of configurational assignment.
复制标题
3-羟基-2,4,6-三甲基庚酸的四种非对映异构体的不对称合成：构型分配的证明。
DOI：
10.1021/jo034738l
复制
发表时间：
2003
期刊：
影响因子：
--
通讯作者：
Lipton,MarkA
中科院分区：
文献类型：
--
作者：
Turk,JeffreyA;Visbal,GonzaloS;Lipton,MarkA
3-羟基-2,4,6-三甲基庚酸 (2R,3R,4R)、(2S,3R,4R)、(2S,3R,4S) 和 (2R,3R,4S)（卡利佩汀 A 和 D 的脂肪酸成分）的四种独特非对映体，由市售 (+)- 和 (-)- 伪麻黄碱丙酰胺分 6 步合成，平均 59%总产量。所得异构体与天然片段的 1 H 和 13 C NMR和旋光度数据的比较明确地验证了天然异构体的构型指定为(2R,3R,4R)。
Four unique diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid(2R,3R,4R), (2S,3R,4R), (2S,3R,4S), and (2R,3R,4S)the fatty acid component of callipeltin A and D, have been synthesized from commercially available (+)- and (−)-pseudoephedrine propionamide in 6 steps and 59% average overall yield. Comparison of the1H and13C NMR and optical rotation data of the resulting isomers with the natural fragment unambiguously verifies the configurational assignment of the natural isomer as (2R,3R,4R).