Ye Jian-Liang, Liu Yang, Yang Zhi-Ping, Huang Pei-Qiang
Department of Chemistry, Fujian Provincial Key Laboratory of Chemical Biology, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China.
Chem Commun (Camb). 2016 Jan 11;52(3):561-3. doi: 10.1039/c5cc07480k. Epub 2015 Nov 5.
The asymmetric total synthesis of (+)-N-acetyl norloline, the putative biogenic precursor of all known loline alkaloids, has been achieved in 12 steps from commercially available (R)-glyceraldehyde acetonide. The synthesis relies on the Rassu/Casiraghi's vinylogous aldol reaction, an intramolecular oxa-heteroconjugate addition and a reductive amination to establish the four contiguous stereogenic centers and construct the strained oxygen-bridge under mild conditions.
从市售的（R）-甘油醛丙酮化物出发，经12步反应实现了（+）-N-乙酰去甲洛林的不对称全合成，（+）-N-乙酰去甲洛林是所有已知洛林生物碱假定的生物合成前体。该合成方法依赖于拉苏/卡西拉吉的插烯羟醛反应、分子内氧杂-杂共轭加成和还原胺化反应，在温和条件下构建四个相邻的手性中心并形成张力氧桥。
