4684-32-6Relevant academic research and scientific papers
Total Synthesis of (-)-Picrinine, (-)-Scholarisine C, and (+)-5-β-Methoxyaspidophylline
Zou, Peng,Yang, Hongjian,Wei, Jian,Wang, Taimin,Zhai, Hongbin
, p. 6836 - 6840 (2021)
The first asymmetric total synthesis of three picrinine-type akuammiline alkaloids, (-)-picrinine, (-)-scholarisine C, and (+)-5-β-methoxyaspidophylline, has been accomplished. The synthesis features an efficient acid-promoted oxo-bridge ring-opening and further carbonyl O-cyclization to assemble the furoindoline scaffold, an unusual Dauben-Michno oxidation to construct the requisite α,β-unsaturated aldehyde functionality, and a nickel-mediated reductive Heck reaction to forge the [3.3.1]-azabicyclic core.
Total synthesis of the akuammiline alkaloid picrinine
Smith, Joel M.,Moreno, Jesus,Boal, Ben W.,Garg, Neil K.
supporting information, p. 4504 - 4507 (2014/04/17)
We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product's carbon framework, and a series of delicate late-stage transformations to complete the synthesis. Our synthesis of picrinine also constitutes a formal synthesis of the related polycyclic alkaloid strictamine.
