Synthesis of Deoxyaminosugar Cyclohexyl-L-callipeltose and Its Diastereomer Using Pd-Catalyzed Asymmetric Hydroalkoxylation
SCIE
SCOPUS
- Title
- Synthesis of Deoxyaminosugar Cyclohexyl-L-callipeltose and Its Diastereomer Using Pd-Catalyzed Asymmetric Hydroalkoxylation
- Authors
- Lee, Sukhyun; Rhee, Young Ho
- Date Issued
- 2019-07
- Publisher
- AMER CHEMICAL SOC
- Abstract
- Cyclohexyl-L-callipeltose, an aminodeoxysugar subunit of Callipeltoside A, was synthesized in six steps and 40% overall yield from readily available (S)-4-methylpent-4-en-2-ol and cyclohexyloxyallene. The signature step is represented by Pd-catalyzed asymmetric intermolecular hydroalkoxylation that generates the key dihydropyran intermediate upon combination with the ring-closing metathesis reaction. Notably, an unnatural diastereomer of the target compound could also be obtained with comparable efficiency simply by using the enantiomeric ligand.
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/100234
- DOI
- 10.1021/acs.joc.9b01059
- ISSN
- 0022-3263
- Article Type
- Article
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, vol. 84, no. 14, page. 9353 - 9357, 2019-07
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