Department of Chemistry, The University of Vermont, 82 University Place, Burlington, Vermont 05405, USA.
Org Lett. 2010 Jan 15;12(2):205-7. doi: 10.1021/ol902455y.
Total syntheses of the Lycopodium alkaloids nankakurines A and B have been accomplished in 6 and 7 steps, respectively, via a sequence that passes through a third Lycopodium alkaloid, luciduline, and forgoes the use of protecting groups on nitrogen. Key features include a short preparation of luciduline followed by a concise and stereoselective aminoallylation/ring-closing metathesis protocol to fashion the spiropiperidine ring common to nankakurines A and B.
已经分别通过 6 步和 7 步反应完成了石松生物碱纳康灵 A 和 B 的全合成,该序列经过了第三种石松生物碱亮氨酸,并避免了在氮上使用保护基团。关键特点包括亮氨酸的简短制备,以及随后进行的简洁和立体选择性的氨烯丙基化/环化复分解反应,以形成纳康灵 A 和 B 共有的螺哌啶环。