State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou, 730000, P. R. China.
J Org Chem. 2014 Jan 3;79(1):122-7. doi: 10.1021/jo4023588. Epub 2013 Nov 27.
An efficient formal synthesis of (±)-cycloclavine is achieved in seven steps and 27% overall yield from the known 2-(4-bromo-1-tosyl-1H-indol-3-yl)acetaldehyde. Key features include an iron(III)-catalyzed aza-Cope-Mannich cyclization and an intramolecular Heck reaction or a self-terminating 6-exo-trig aryl radical-alkene cyclization.
(±)-环克拉维因的高效形式合成以 2-(4-溴-1-对甲苯磺酰基-1H-吲哚-3-基)乙醛为原料,经 7 步反应,总收率为 27%。关键步骤包括铁(III)催化的氮杂-Cope-Mannich 环化和分子内 Heck 反应或自终止的 6-endo-trig 芳基自由基-烯烃环化。