Kobayashi Shoji, Hori Makiko, Wang Guang Xing, Hirama Masahiro
Department of Chemistry, Graduate Schools of Science, Tohoku University, Sendai 980-8578, Japan.
J Org Chem. 2006 Jan 20;71(2):636-44. doi: 10.1021/jo052031o.
[reaction: see text] An efficient route to the neocarzinostatin chromophore aglycon has been developed. The present strategy involves a stereoselective intramolecular acetylide-aldehyde cyclization to form the C5-C6 bond, followed by efficient installation of alpha-epoxide, naphthoate, and carbonate functionalities. The C8-C9-olefin was introduced by using the Martin sulfurane dehydration reaction to furnish the highly reactive aglycon.
[反应：见正文] 已开发出一条通往新制癌菌素发色团苷元的有效路线。目前的策略包括立体选择性分子内乙炔 - 醛环化以形成C5 - C6键，随后高效引入α - 环氧化物、萘甲酸酯和碳酸酯官能团。通过使用马丁硫烷脱水反应引入C8 - C9 - 烯烃以得到高反应活性的苷元。
