Concise, stereoselective approach to the spirooxindole ring system of citrinadin A.
The spirooxindole ring system of citrinadin A has been synthesized with excellent control over the absolute stereochemistry at the spirocenter. The key step involves a novel diastereoselective DMDO-mediated oxidative rearrangement employing an 8-phenylmenthol chiral auxiliary on the indole nitrogen.
Pettersson
Martin
M
Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712, USA.
Knueppel
Daniel
D
Martin
Stephen F
SF
D000970:Antineoplastic Agents / Q000138:chemical synthesis; D026121:Indole Alkaloids; D008958:Models, Molecular; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis*; D014633:Valine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000970:Antineoplastic Agents; D026121:Indole Alkaloids; D011807:Quinolizines; C503673:citrinadin A; D014633:Valine