Journal article
Enantioselective synthesis of (+)-kjellmanianone
Tetrahedron, v 47(2), pp 173-182
1991
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
An asymmetric synthesis of the highly oxygenated cyclopentanoid antibiotic (+)-kjellmanianone (
1) has been achieved. The key step entailed enantioselective hydroxylation of the prochiral sodium enolate of β-keto ester
2 with the new, enantiomerically pure N-sulfonyloxaziridine
7b, affording
1 in 68.5% ee (60% yield). Possible transition state structures for the asymmetric oxidation are evaluated.
An symmetric synthesis of the highly oxygenated cyclopentanoid antibiotic (+)-kjellmanianone (
1) has been achieved. The key step entailed enantioselective hydroxylation of the prochiral sodium enolate of β-keto ester
2 with the new, enantiomerically pure N-sulfonyloxaziridine
7b, affording
1 in 68.5% ee.
Metrics
Details
- Title
- Enantioselective synthesis of (+)-kjellmanianone
- Creators
- Bang-Chi Chen - Drexel UniversityMichael C. Weismiller - Drexel UniversityFranklin A. Davis - Drexel UniversityDiane Boschelli - Monell Chemical Senses CenterJames R. Empfield - Monell Chemical Senses CenterAmos B. Smith - Monell Chemical Senses Center
- Publication Details
- Tetrahedron, v 47(2), pp 173-182
- Publisher
- Elsevier
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- [Retired Faculty]
- Web of Science ID
- WOS:A1991EN60100001
- Scopus ID
- 2-s2.0-0026089158
- Other Identifier
- 991019173832704721
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- Collaboration types
- Domestic collaboration
- Web of Science research areas
- Chemistry, Organic