An approach to the synthesis of stenine.
A type 2 N-acylnitroso intramolecular Diels-Alder reaction followed by reductive N-O bond cleavage formed the B and C rings of the Stemona alkaloid stenine. Further elaboration provided the functionalized tricyclic core.
Zhu
Liang
L
Department of Chemistry, Natural Sciences 1102, University of California Irvine, Irvine, California 92697, USA.
Lauchli
Ryan
R
Loo
Mandy
M
Shea
Kenneth J
KJ
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; C441784:stenine