Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine
- Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine
- 이백경; 최환근; 노은주; 이원구; 심태보
- (-)-8-epi-swainsonine; Indolizidine alkaloids; Total synthesis; Aziridine; Natural product
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- VOL 54, NO 6, 553-556
- An efficient synthesis of (−)-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 (−)-8-epi-swainsonine.
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