Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach

Title
Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach
Authors
윤호종조경선심태보
Keywords
(+)-lentiginosine; 천연물 전합성
Issue Date
2014-04
Publisher
Tetrahedron, asymmetry
Citation
VOL 25, NO 6-7, 497-502
Abstract
The synthesis of the indolizidine alkaloid, (+)-lentiginosine, is described. A key feature of the preparative route is the efficient and stereoselective construction of a dihydroxylated pyrrolidine via Sharpless asymmetric dihydroxylation of an aziridine-enoate, which was prepared from commercially available 1-(S)-α-methylbenzylaziridine-2-methanol. In addition, a regioselective aziridine-to-pyrrolidinone ring expansion process followed by a Wittig olefination was employed to construct a late stage pyrrolidine intermediate that was transformed into (+)-lentiginosine.
URI
http://pubs.kist.re.kr/handle/201004/50439
ISSN
09574166
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KIST Publication > Article
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