单萜吡啶生物碱Aucubinine A的合成

Synthesis of Monoterpene Pyridine Alkaloid Aucubinine A

AucubinineA是自aucubin在人类大肠杆菌存在时的代谢产物中分离得到的一种单萜生物碱 .本课题组实现了起始于 4 氢 5 羟基 3 亚甲基 5H 环戊二烯 [2 ,1 c]吡啶 ( 6)对aucubinineA的首次合成 ,总产率为 3 0 % .硼氢化以及随后的在碱性介质中的氧化将 6转化为两个非对映异构的二醇 7。

Aucubinine A, a monoterpene alkaloid isolated from the metabolites of aucubin in the presence of human intestinal bacteria, has been synthesized from 4-hydro-5-hydroxyl-3-methylidene-5H-cyclopentadieno[2,1-c]pyridine (6) in 30% overall yield. Hydroboration followed by oxidation in basic medium converted 6 to diastereomeric diols 7, which were subjected to selective benzylic oxidation to form aucubinine A.