当前位置: X-MOL 学术Tetrahedron Lett. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Stereodivergent synthesis of cyclic γ-aminobutyric acid – GABA analogues
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2019-01-04 , DOI: 10.1016/j.tetlet.2019.01.005
Andrej Ďuriš , Dušan Berkeš , Pavol Jakubec

A novel synthetic route towards two series of enantiomerically pure cyclic analogues of 2,3-cis- and 2,3-trans-γ-aminobutyric acid (GABA) was developed. The route is based on the elongation and stereodivergent manipulation of a readily accessible enantiomerically pure γ-substituted α-aminolactone. The five-step route towards the 2,3-cis-substituted GABA analogues was achieved via straightforward carbon chain extension of the lactone using a non-classical Wittig reaction followed by chemoselective reduction and a protecting group switch. The five-step route towards the 2,3-trans-substituted GABA analogues employed elongation of the same aminolactone using a Horner-Wadsworth-Emmons reaction and highly stereoselective intramolecular oxa-Michael addition as the key synthetic manipulations. Altogether this chemistry has allowed the stereodivergent preparation of a novel class of GABA analogues in two diastereomeric series.



中文翻译:

环状γ-氨基丁酸– GABA类似物的立体发散合成

提出了一条新的合成路线,该路线指向两个对映体纯的2,3-顺式和2,3-反式-γ-氨基丁酸(GABA)系列环状类似物。该途径基于易于获得的对映体纯的γ-取代的α-氨基内酯的延伸和立体发散操纵。朝向2,3-五步路径顺式-取代的GABA类似物达到通过使用一种非经典Wittig反应,接着化学选择性还原内酯的直接的碳链延长和保护基团的开关。通往2,3-反式的五步路线-取代的GABA类似物利用Horner-Wadsworth-Emmons反应和高度立体选择性的分子内氧杂-Michael加成作为关键的合成操作,延长了相同的氨基内酯。总的来说,这种化学方法允许立体发散地制备两种非对映异构体系列的新型GABA类似物。

更新日期:2019-01-04
down
wechat
bug