Department of Chemistry, University of Zurich , 8057 Zurich, Switzerland.
Department of Chemistry, University of Basel , 4056 Basel, Switzerland.
Org Lett. 2017 Feb 3;19(3):548-551. doi: 10.1021/acs.orglett.6b03716. Epub 2017 Jan 17.
The synthesis of the Securinega alkaloid secu'amamine E (ent-virosine A) has been accomplished for the first time in 12 steps and 8.5% overall yield. In addition, bubbialine has been prepared and characterized. These two alkaloids and bubbialidine, all featuring an azabicyclo[2.2.2]octane core, were rearranged to their azabicyclo[3.2.1]octane congeners, a framework found in many Securinega alkaloids. These experiments suggest that azabicyclo[2.2.2]octane derivatives could serve as intermediates in the biosynthesis of the rearranged azabicyclo[3.2.1]octane products.
首次以 12 步和 8.5%的总收率完成了 Securinega 生物碱 secu'amamine E（ent-virosine A）的合成。此外，还制备和表征了 bubbialine。这两种生物碱和具有氮杂双环[2.2.2]辛烷核心的 bubbialidine 都被重排成它们的氮杂双环[3.2.1]辛烷同系物，这是许多 Securinega 生物碱中的一个骨架。这些实验表明，氮杂双环[2.2.2]辛烷衍生物可以作为重排氮杂双环[3.2.1]辛烷产物生物合成的中间体。
