An expeditious total synthesis of (+/-)-stenine.
(+/-)-Stenine was synthesized in eight steps from a known ketophosphonate reagent. The key step was an exo-selective Diels-Alder/intramolecular Schmidt domino reaction that afforded three of the four rings and four stereocenters in a single reaction.
Zeng
Yibin
Y
Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, Lawrence, Kansas 66045-7852, USA.
Aubé
Jeffrey
J
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000470:Alkaloids; C441784:stenine