(15S,16S,19S,20R,34S)和(15R,16R,19R,20S,34S)氮杂Solamin类似物的合成

Syntheses of (15R,16R,19R,20S,34S) and (15S,16S,19S,20R,34S) Aza-solamin

以手性四氢吡咯片段3a和3b为起始原料,采用汇聚式合成策略,完成氮杂Solamin类似物(threo-trans-erythro)的两个对应的光学异构体2a(15S,16S,19S,20R,34S)和2b(15R,16R,19R,20S,34S)的不对称合成.化合物的结构以及四氢吡咯片段的立体构型均通过NMR波谱解析的方法得到确证.这两个非对映异构体具有相近的体外抗肿瘤活性.

A convergent synthesis of two possible diastereomers of aza-solamin （threo-trans-erythro） （2a and 2b） , which possessed pyrrolidine ring in place of THF ring of solamin, was accomplished. The key building block 5a and 9a were originated from chrial starting material. The stereochemistry of pyrrolidine core unit was determined by ^1H NMR spectroscopic analysis. The preliminary results of in vitro test against A-549 and HCT- 116 cell lines show that both compounds have almost the same activity.