Bringmann Gerhard, Gulder Tanja, Reichert Matthias, Meyer Frank
Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany.
Org Lett. 2006 Mar 16;8(6):1037-40. doi: 10.1021/ol052946p.
[reaction: see text] The first total synthesis of an N,C-coupled naphthylisoquinoline alkaloid-ancisheynine-was achieved by condensing a monocyclic diketone or the respective benzopyrylium salt with an aminonaphthalene. The presence of a rotationally hindered axis in ancisheynine was demonstrated by resolution of its two atropo-enantiomers by HPLC on a chiral phase with LC-CD coupling. The assignment of their axial configurations succeeded by quantum chemical CD calculations.
[反应：见正文] 通过将单环二酮或相应的苯并吡喃盐与氨基萘缩合，首次实现了N，C偶联萘基异喹啉生物碱——安西海宁的全合成。通过在手性相上采用LC-CD联用的HPLC拆分其两种阻转对映体，证明了安西海宁中存在一个旋转受阻轴。通过量子化学CD计算成功确定了它们的轴向构型。
