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Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene
The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the...
| Autores principales: | , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
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Beilstein-Institut
2016
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979643/ https://www.ncbi.nlm.nih.gov/pubmed/27559385 http://dx.doi.org/10.3762/bjoc.12.129 |
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| author | Seidl, Frederick J Burns, Noah Z |
| author_facet | Seidl, Frederick J Burns, Noah Z |
| author_sort | Seidl, Frederick J |
| collection | PubMed |
| description | The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (−)-anverene. |
| format | Online Article Text |
| id | pubmed-4979643 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2016 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-49796432016-08-24 Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene Seidl, Frederick J Burns, Noah Z Beilstein J Org Chem Full Research Paper The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (−)-anverene. Beilstein-Institut 2016-07-01 /pmc/articles/PMC4979643/ /pubmed/27559385 http://dx.doi.org/10.3762/bjoc.12.129 Text en Copyright © 2016, Seidl and Burns https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
| spellingShingle | Full Research Paper Seidl, Frederick J Burns, Noah Z Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene |
| title | Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene |
| title_full | Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene |
| title_fullStr | Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene |
| title_full_unstemmed | Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene |
| title_short | Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene |
| title_sort | selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979643/ https://www.ncbi.nlm.nih.gov/pubmed/27559385 http://dx.doi.org/10.3762/bjoc.12.129 |
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