State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China.
J Org Chem. 2013 Jun 21;78(12):6154-62. doi: 10.1021/jo4007943. Epub 2013 Jun 13.
Transannular reductive rearrangement of bridged cyclic α-amino ketones led to the aza-tricyclic frameworks azepinoindole, hydrolulolidine, and hydrojulolidine of the typical alkaloids of Stemona, Aspidosperma, and Lycopodium, respectively. This facile approach demonstrates the potential applicability of the Clemmensen-Clemo-Prelog-Leonard reductive rearrangement of tricyclic α-amino ketones for the aza-heterocycle synthesis.
桥环α-氨基酸酮的跨环还原重排导致了斯藤酮、长春花和石松典型生物碱的氮杂三环框架氮杂吲哚、水合六氢吲哚啉和水合六氢吲哚的形成。这种简便的方法证明了三环α-氨基酸酮的克莱门森-克莱蒙诺-普雷洛格-伦纳德还原重排对氮杂杂环合成的潜在适用性。
