Nilsson Bradley L, Overman Larry E, Read de Alaniz Javier, Rohde Jason M
Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, California 92697-2025, USA.
J Am Chem Soc. 2008 Aug 27;130(34):11297-9. doi: 10.1021/ja804624u. Epub 2008 Aug 2.
Total syntheses of (+)-nankakurine A (2) and (+)-nankakurine B (3) were accomplished by a sequence that employs an intramolecular dipolar cycloaddition of an azomethine imine intermediate to form the azatricyclic moiety and establish the relative configuration of the spiropiperidine ring. These syntheses, together with the synthesis of the originally purported structure 1 of nankakurine A, rigorously establish the relative and absolute configuration of these structurally unusual Lycopodium alkaloids. The syntheses are sufficiently concise that gram quantities of (+)-nankakurine A (2) and (+)-nankakurine B (3) will be available for further biological studies.
(+)-南卡库林A（2）和(+)-南卡库林B（3）的全合成是通过一系列反应完成的，该反应利用甲亚胺亚胺中间体的分子内偶极环加成反应来形成氮杂三环部分并确定螺哌啶环的相对构型。这些合成方法，连同最初推测的南卡库林A结构1的合成，严格确定了这些结构异常的石松生物碱的相对和绝对构型。这些合成方法足够简洁，以至于可以获得克级量的(+)-南卡库林A（2）和(+)-南卡库林B（3）用于进一步的生物学研究。
