Syntheses of the Stemona alkaloids (+/-)-stenine, (+/-)-neostenine, and (+/-)-13-epineostenine using a stereodivergent Diels-Alder/azido-Schmidt reaction.
A tandem Diels-Alder/azido-Schmidt reaction sequence provides rapid access to the core skeleton shared by several Stemona alkaloids including stenine, neostenine, tuberostemonine, and neotuberostemonine. The discovery and evolution of inter- and intramolecular variations of this process and their applications to total syntheses of (+/-)-stenine and (+/-)-neostenine are described. The stereochemical outcome of the reaction depends on both substrate type and reaction conditions, enabling the preparation of both (+/-)-stenine and (+/-)-neostenine from the same diene/dienophile combination.
Frankowski
Kevin J
KJ
Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66045-7582, USA.
Golden
Jennifer E
JE
Zeng
Yibin
Y
Lei
Yao
Y
Aubé
Jeffrey
J
D000470:Alkaloids / Q000138:chemical synthesis*; D041901:Stemonaceae / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; C441784:stenine