Total Synthesis of (−)-Picrinine, (−)-Scholarisine C, and (+)-5-β-Methoxyaspidophylline
Peng Zou, Hongjian Yang, Jian Wei, Taimin Wang, Hongbin Zhai
Abstract
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.
Topics & Concepts
ChemistryTotal synthesisStereochemistryCombinatorial chemistryMedicinal chemistryChemical synthesis and alkaloidsPhytochemistry and Bioactivity StudiesPhytochemical compounds biological activities