Application of the intramolecular Schmidt reaction to the asymmetric synthesis of (−)-indolizidine 209B from pulegone
Application of the intramolecular Schmidt reaction to the asymmetric synthesis of (−)-indolizidine 209B from pulegone
复制标题
DOI：
10.3987/com-92-s(t)113
复制
发表时间：
1993-05
期刊：
影响因子：
0.6
通讯作者：
J. Aubé;Pat S. Rafferty;G. Milligan
中科院分区：
文献类型：
--
作者：
J. Aubé;Pat S. Rafferty;G. Milligan
从天然产物胡薄荷酮出发，合成了对映体纯的吲哚里西啶生物碱209 B。关键步骤是通过烷基叠氮化物与环酮的分子内施密特反应形成双环内酰胺。以21.9%的总收率完成了11锅合成
A synthesis of enantiomerically pure indolizidine alkaloid 209B, beginning from naturally occurring pulegone, is described. The key step is the formation of a bicyclic lactam via the intramolecular Schmidt reaction of an alkyl azide with a cyclic ketone. The 11-pot synthesis was accomplished in an overall yield of 21.9%