去甲粉防己碱ACDE环系的直接和简短构建

Direct and short construction of the ACDE ring system of daphenylline.

作者信息

Wang Wei, Li Guo-Ping, Wang Shao-Feng, Shi Zi-Fa, Cao Xiao-Ping

机构信息

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000 (P. R. China).

出版信息

Chem Asian J. 2015 Feb;10(2):377-82. doi: 10.1002/asia.201403152. Epub 2014 Nov 25.

DOI:10.1002/asia.201403152

PMID:25425355

Abstract

Daphenylline, a novel daphniphyllum alkaloid, boasts a fused and bridging ring system coupled with six stereogenic centers. Here we present a direct and short construction of the ACDE ring system of daphenylline from the known 3-(2-bromophenyl)propanal in 10 steps and 17 % overall yield. The synthesis features an iron(III)-catalyzed aza-Cope-Mannich reaction, a self-terminating 6-exo-trig aryl radical-alkene cyclization and an intramolecular Friedel-Crafts acylation.

摘要

瑞香灵，一种新型的瑞香科生物碱，具有稠合和桥连的环系以及六个立体中心。在此，我们报道了一种从已知的3-(2-溴苯基)丙醛出发，经10步反应、总产率为17%直接且简短地构建瑞香灵ACDE环系的方法。该合成方法的特点包括铁(III)催化的氮杂-Cope-曼尼希反应、自终止的6-外向-芳基自由基-烯烃环化反应以及分子内傅克酰基化反应。