Satcharoen Vachiraporn, McLean Neville J, Kemp Stephen C, Camp Nicholas P, Brown Richard C D
School of Chemistry, University of Southampton, Highfield, Southampton, UK.
Org Lett. 2007 May 10;9(10):1867-9. doi: 10.1021/ol070255i. Epub 2007 Apr 13.
An enantioselective synthesis of (-)-galanthamine has been realized in 11 linear steps starting from isovanillin. A Mitsunobu aryl ether forming reaction was used to assemble the galanthamine backbone, which was stitched together using enyne ring-closing metathesis, Heck, and N-alkylation reactions affording the tetracyclic ring system. Control of relative and absolute stereochemistry was derived from an easily accessible enantiomerically enriched propargylic alcohol 13.
从异香草醛出发，通过11步线性反应实现了（-）-加兰他敏的对映选择性合成。利用Mitsunobu芳基醚形成反应构建加兰他敏骨架，该骨架通过烯炔关环复分解反应、Heck反应和N-烷基化反应拼接在一起，得到四环环系。相对和绝对立体化学的控制源自易于获得的对映体富集的炔丙醇13。
