Stereoselective Synthesis of (+)-Polyoxamic Acid Starting with a Chiral Aziridine
- Authors
- Yoon, Hojong; Sim, Taebo
- Issue Date
- 2-12월-2013
- Publisher
- GEORG THIEME VERLAG KG
- Keywords
- polyhydroxylated amino acid; (+)-polyoxamic acid; natural product synthesis; chiral aziridine; asymmetric dihydroxylation
- Citation
- SYNTHESIS-STUTTGART, v.45, no.23, pp.3276 - 3280
- Indexed
- SCIE
SCOPUS
- Journal Title
- SYNTHESIS-STUTTGART
- Volume
- 45
- Number
- 23
- Start Page
- 3276
- End Page
- 3280
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/101319
- DOI
- 10.1055/s-0033-1338545
- ISSN
- 0039-7881
- Abstract
- An efficient and stereoselective synthesis of (+)-polyoxamic acid was developed. The route starts with the commercially available 1-(R)--methylbenzylaziridine-2-methanol, a substance that has not been used previously as a starting material for the preparation of this target. The route also features the use of a stereocontrolled Sharpless asymmetric dihydroxylation reaction, promoted by AD-mix-, which is followed by a regioselective aziridine ring-opening process, to generate the basic skeleton of target natural product. Subsequent oxidation and global deprotection produces (+)-polyoxamic acid.
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Collections - Graduate School > KU-KIST Graduate School of Converging Science and Technology > 1. Journal Articles
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