Brenneman Jehrod B, Martin Stephen F
Department of Chemistry and Biochemistry, The University of Texas, Austin, TX 78712, USA.
Org Lett. 2004 Apr 15;6(8):1329-31. doi: 10.1021/ol049631e.
A concise synthesis of the potent nAChR agonist (+)-anatoxin-a (1) has been completed in a series of only nine chemical operations and 27% overall yield from commercially available D-methyl pyroglutamate (4). The synthesis features a novel procedure for the diastereoselective preparation of cis-2,5-disubstituted pyrrolidines leading to 10, which underwent an intramolecular enyne metathesis to afford a bridged azabicyclic intermediate that was transformed into 1. [reaction: see text]
已通过一系列仅九步化学操作，从市售的D-甲基焦谷氨酸（4）以27%的总收率完成了强效烟碱型乙酰胆碱受体激动剂（+）-anatoxin-a（1）的简洁合成。该合成的特点是一种非对映选择性制备顺式-2,5-二取代吡咯烷生成10的新方法，10经过分子内烯炔复分解反应得到一个桥连氮杂双环中间体，该中间体再转化为1。[反应：见正文]
