Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine

Title
Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine
Authors
이백경최환근노은주이원구심태보
Keywords
(-)-8-epi-swainsonine; Indolizidine alkaloids; Total synthesis; Aziridine; Natural product
Issue Date
2013-02
Publisher
Tetrahedron letters
Citation
VOL 54, NO 6, 553-556
Abstract
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.
URI
http://pubs.kist.re.kr/handle/201004/44488
ISSN
00404039
Appears in Collections:
KIST Publication > Article
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