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Metathesis-Based de novo synthesis of noviose
- The rare carbohydrate L-(+)-noviose was synthesized from enantiomerically pure L-lactate. The configuration at C-4 was established by diastereoselective nucleophilic addition to an in-situ-generated lactaldehyde. The resulting homoallylic alcohol was further transformed into a set of ring-closing metathesis (RCM) precursors. These compounds were converted into noviose in few steps using RCM and RCM-allylic-oxidation sequences.
| Author details: | Bernd SchmidtORCiDGND, Sylvia Hauke |
|---|---|
| DOI: | https://doi.org/10.1002/ejoc.201301615 |
| ISSN: | 1434-193X |
| ISSN: | 1099-0690 |
| Title of parent work (English): | European journal of organic chemistry |
| Publisher: | Wiley-VCH |
| Place of publishing: | Weinheim |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2014 |
| Publication year: | 2014 |
| Release date: | 2017/03/27 |
| Tag: | Allylic oxidation; Carbohydrates; Metathesis; Oxygen heterocycles; Ruthenium |
| Volume: | 2014 |
| Issue: | 9 |
| Number of pages: | 10 |
| First page: | 1951 |
| Last Page: | 1960 |
| Funding institution: | Deutsche Forschungsgemeinschaft (DFG) [1095/6-2] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
