Pettersson Martin, Knueppel Daniel, Martin Stephen F
Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712, USA.
Org Lett. 2007 Oct 25;9(22):4623-6. doi: 10.1021/ol702132v. Epub 2007 Oct 6.
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.
柠檬苦素A的螺环氧化吲哚环系统已被合成,对螺中心的绝对立体化学具有出色的控制。关键步骤涉及在吲哚氮上使用8-苯基薄荷醇手性助剂的新型非对映选择性DMDO介导的氧化重排。