Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach
- Authors
- Yoon, Hojong; Cho, Kyung Seon; Sim, Taebo
- Issue Date
- 15-4월-2014
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Citation
- TETRAHEDRON-ASYMMETRY, v.25, no.6-7, pp.497 - 502
- Indexed
- SCIE
SCOPUS
- Journal Title
- TETRAHEDRON-ASYMMETRY
- Volume
- 25
- Number
- 6-7
- Start Page
- 497
- End Page
- 502
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/98759
- DOI
- 10.1016/j.tetasy.2014.02.009
- ISSN
- 0957-4166
- 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)-alpha-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. (c) 2014 Elsevier Ltd. All rights reserved.
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Collections - Graduate School > KU-KIST Graduate School of Converging Science and Technology > 1. Journal Articles
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