Synthesis of L-2-(2-carboxy-4-methylenecyclopentyl)glycines (CPGs). Novel conformationally restricted glutamate analogues
作者:S. Raghavan、Michiko Ishida、Haruhiko Shinozaki、Koji Nakanishi、Yasufumi Ohfune
DOI:10.1016/s0040-4039(00)73855-x
日期:1993.9
Three diastereomers 1, 2, and 4 of a new glutamate analogue incorporating a 5-membered ring were synthesized in a stereocontrolled manner. 1′R-Isomers 2 and 4 were constructed from the α,β-unsaturated 2,2,2-trifluoroethyl esters 5b and 10b by a [3+2] cycloaddition with a Pd-trimethylenemethane (TMM) complex. The 1′S isomer 1 was synthesized by a 1,4-addition of TMM equivalent to the α,β-unsaturated
三个非对映体1,2,和4结合有5元环的新的谷氨酸类似物的立体控制的方式合成。1' - [R -异构体2和4分别来自α构造,β不饱和2,2,2-三氟乙基酯5B和图10b通过[3 + 2]环加成与Pd的trimethylenemethane(TMM)络合物。1 'S异构体1是通过与α,β-不饱和甲酯10a等效的TMM的1,4-加成合成的。折叠异构体4 在生理学上被表征为哺乳动物中枢神经系统中的有效的海藻酸盐受体激动剂。