百部酰胺的全合成研究进展

百部酰胺(Stemoamide)是从百部科植物对叶百部Stemona tuberosa L.根部分离得到的天然产物。百部化合物在中医药应用中具有镇咳和驱虫的功效。其结构是γ-丁内酯并氮杂薁环的三环体系,有四个连续的手性中心。文章综述了目前国内外对百部酰胺Stemoamide的全合成方法,着重从成环顺序的角度进行论述,介绍了(Diels-Alder)-(逆-Diels-Alder)策略、自由基环化、RCM环化、分子内的Barbier反应和仿生亚胺离子环化等方法在百部酰胺全合成中的应用。

Progress of Syntheses of Stemoamide

Stemoamide was isolated from the roots and rhizomes of Stemonaceous plants. The roots of Stemona tuberosa L. and related Sternona species （Stemonaceae） are used in Chinese traditional medicine as antitussive agents as well as insecticides and anthelmintics. The structure of stemoamide was determined by spectroscopic methods to contain a pyrrolo[1,2-a]azepine ring system fused to a γ-butyrolactone ring with four contiguous stereogenic centers. The progress towards the total synthesis of stemoamide are reviewed according to the order of ring formation, and the （Diels-Alder）-（retro-Diels-Alder） reaction, the radical addition-cyclization, ring closing metathesis, intramolecular Barbier reaction, and more recently a biomimetic iminium cyclization strategy used in these total synthesis are summarized.