Semghouli Anas, Remete Attila M, Kiss Loránd
Institute of Pharmaceutical Chemistry, University of Szeged Eötvös u. 6 H-6720 Szeged Hungary.
Institute of Organic Chemistry, Stereochemistry Research Group, Research Centre for Natural Sciences Magyar tudósok krt. 2 H-1117 Budapest Hungary
RSC Adv. 2023 Jul 27;13(33):22769-22776. doi: 10.1039/d3ra03866a. eCollection 2023 Jul 26.
The synthesis of some novel functionalized fused-ring β-amino lactones and lactams with multiple chiral centers has been attempted from readily available strained bicyclic β-amino acids a stereocontrolled synthetic route. The key step was ring-rearrangement metathesis of allyl/propargyl esters or -allylated/-propargylated amides of (oxa)norbornene β-amino acids. The RRM transformations [ring-opening metathesis (ROM)/ring-closing metathesis (RCM) or ring-opening metathesis (ROM)/ring-closing enyne metathesis (RCEYM)] have been investigated using some commercially available catalysts. Importantly, the procedure used in this synthetic process does not affect the configurations of the chiral centers. This means that the structure of the starting (oxa)norbornene β-amino acids predetermines the configuration of the formed products.
已尝试从容易获得的具有张力的双环β-氨基酸通过立体控制的合成路线合成一些具有多个手性中心的新型官能化稠环β-氨基内酯和内酰胺。关键步骤是（氧杂）降冰片烯β-氨基酸的烯丙基/炔丙基酯或烯丙基化/炔丙基化酰胺的环重排复分解反应。使用一些市售催化剂研究了RRM转化[开环复分解（ROM）/闭环复分解（RCM）或开环复分解（ROM）/闭环烯炔复分解（RCEYM）]。重要的是，该合成过程中使用的方法不会影响手性中心的构型。这意味着起始（氧杂）降冰片烯β-氨基酸的结构预先决定了所形成产物的构型。
