1371592-99-2Relevant academic research and scientific papers
Divergent total syntheses of (-)-aspidospermine and (+)-spegazzinine
Lajiness, James P.,Jiang, Wanlong,Boger, Dale L.
, p. 2078 - 2081 (2012/06/18)
Divergent total syntheses of (+)-spegazzinine (1) and (-)-aspidospermine (2) and their extensions to the synthesis of C19-epi-aspidospermine and C3-epi-spegazzinine are detailed, confirming the relative stereochemistry and establishing the absolute configuration of (+)-spegazzinine. A powerful intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of a 1,3,4-oxadiazole provided the pentacyclic skeleton and all the requisite stereochemistry of the natural products in a single reaction that forms three rings, four C-C bonds, and five stereocenters.
