Wang Mei-Xiang, Liu Yong, Gao Hong-Yun, Zhang Yan, Yu Chu-Yi, Huang Zhi-Tang, Fleet George W J
Laboratory of Chemical Biology, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China.
J Org Chem. 2003 Apr 18;68(8):3281-6. doi: 10.1021/jo026560t.
A novel approach to heterocyclic enamines has been developed from the formal ring transformation reaction of lactones. The synthesis comprises consecutive Reformatsky reaction of lactones and mesylation of the resulting mixture of ring-chain tautomers in a one-pot reaction, followed by cyclocondensation reaction with primary amines. The synthetic application of this method was demonstrated by a straightforward preparation of indolizidine compounds via N-(3-bromopropyl)-substituted enamine intermediates. The use of cheap and readily available materials and reagents under very mild conditions renders this formal ring transformation method practical and applicable in the preparation of various heterocyclic enamines that are the precursors for (poly)hydroxylated alkaloid derivatives.
一种从内酯的形式环转化反应开发的新型杂环烯胺方法已经出现。该合成方法包括内酯的连续Reformatsky反应以及所得环链互变异构体混合物在一锅反应中的甲磺酰化，随后与伯胺进行环缩合反应。通过经由N-(3-溴丙基)取代的烯胺中间体直接制备吲哚里西啶化合物，证明了该方法的合成应用。在非常温和的条件下使用廉价且易于获得的材料和试剂，使得这种形式环转化方法在制备各种杂环烯胺方面切实可行且适用，这些杂环烯胺是（多）羟基化生物碱衍生物的前体。
