Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5266632 | Tetrahedron Letters | 2013 | 4 Pages |
Abstract
An efficient synthesis of (â)-8-epi-swainsonine, starting from a commercially available 1-(R)-α-methylbenzylaziridine-2-methanol, was developed. The synthetic route utilizes stereocontrolled Sharpless asymmetric dihydroxylation governed by AD-mix-β followed by an aziridine ring opening-cyclization sequence to generate the five membered N-heterocyclic ring system present in the bicyclic target. A subsequent stereoselective allylation and piperidine ring forming cyclization then produced a precursor that was converted into (â)-8-epi-swainsonine.
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Baeck Kyoung Lee, Hwan Geun Choi, Eun Joo Roh, Won Koo Lee, Taebo Sim,