色胺的不对称溴环化反应及其在环色胺生物碱的合成中的应用

Cyclotryptamine alkaloids are a large family of indole alkaloids with potent biological activities and complex structure. This family of alkaloids are structurally oligomers of hexahydropyrrolo[2,3-b]indole，which are mainly connected through C3-C3' and C3-C7' bonds. By taking advantage of bifunctional organocatalysts to effect asymmetric bromocyclization of tryptamine, chiral 3-bromo-pyrroloindolines could be obtained from different substituted tryptamines. Starting from chiral 3-bromo-pyrroloindolines as building blocks, dimmers and higher-order oligomers of cyclotryptamine alkaloids could be constructed in a stepwise and programmed way, which constitutes an efficient and convenient route to synthesize cyclotryptamine alkaloids.

环色胺生物碱是一类结构复杂、具有很好生物活性的吲哚类生物碱。这一类分子以吡咯并吲哚啉为结构单元通过C3-C3'及C3-C7'键形成的多聚体。通过对有机小分子催化的溴环化反应的研究，筛选合适的双功能小分子催化和其他的反应条件实现色胺的不对称溴环化反应。通过发展的色胺不对称溴环化反应可以出不同取代色胺出发，合成光学活性的3-溴吡咯并吲哚啉分子。以得到的光学活性的3-溴吡咯并吲哚啉为切块，通过逐步连接方法可以高效地合成环色胺生物碱的二聚体及更高阶的多聚体。