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Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one
A short five steps synthesis of the title compound from vanillin is described. The racemic spiroether 7 was obtained in 61% yield and in >99% diastereomeric excess (by (1)H-NMR) from the corresponding phenolic derivative 3 by oxidation with lead (IV) acetate.
| Autores principales: | , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
MDPI
2013
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270225/ https://www.ncbi.nlm.nih.gov/pubmed/23344206 http://dx.doi.org/10.3390/molecules18011174 |
| _version_ | 1783376648957067264 |
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| author | Plourde, Guy L. Scully, Thomas W. |
| author_facet | Plourde, Guy L. Scully, Thomas W. |
| author_sort | Plourde, Guy L. |
| collection | PubMed |
| description | A short five steps synthesis of the title compound from vanillin is described. The racemic spiroether 7 was obtained in 61% yield and in >99% diastereomeric excess (by (1)H-NMR) from the corresponding phenolic derivative 3 by oxidation with lead (IV) acetate. |
| format | Online Article Text |
| id | pubmed-6270225 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2013 |
| publisher | MDPI |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-62702252018-12-14 Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one Plourde, Guy L. Scully, Thomas W. Molecules Article A short five steps synthesis of the title compound from vanillin is described. The racemic spiroether 7 was obtained in 61% yield and in >99% diastereomeric excess (by (1)H-NMR) from the corresponding phenolic derivative 3 by oxidation with lead (IV) acetate. MDPI 2013-01-17 /pmc/articles/PMC6270225/ /pubmed/23344206 http://dx.doi.org/10.3390/molecules18011174 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
| spellingShingle | Article Plourde, Guy L. Scully, Thomas W. Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one |
| title | Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one |
| title_full | Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one |
| title_fullStr | Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one |
| title_full_unstemmed | Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one |
| title_short | Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one |
| title_sort | diastereoselective synthesis of 5-hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one |
| topic | Article |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270225/ https://www.ncbi.nlm.nih.gov/pubmed/23344206 http://dx.doi.org/10.3390/molecules18011174 |
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