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Total Synthesis of Tetrahydrolipstatin and Stereoisomers via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic Alcohols
[Image: see text] A concise enantioselective synthesis of tetrahydrolipstatin (THL) and seven stereoisomers has been achieved. The synthesis of THL was accomplished in 10 steps and 31% overall yield from an achiral ynone. Key to the success of the approach is the use of a bimetallic [Lewis acid](+)[...
| Autores principales: | , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical
Society
2014
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120994/ https://www.ncbi.nlm.nih.gov/pubmed/25004122 http://dx.doi.org/10.1021/ja505639u |
| _version_ | 1782329160340865024 |
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| author | Mulzer, Michael Tiegs, Brandon J. Wang, Yanping Coates, Geoffrey W. O’Doherty, George A. |
| author_facet | Mulzer, Michael Tiegs, Brandon J. Wang, Yanping Coates, Geoffrey W. O’Doherty, George A. |
| author_sort | Mulzer, Michael |
| collection | PubMed |
| description | [Image: see text] A concise enantioselective synthesis of tetrahydrolipstatin (THL) and seven stereoisomers has been achieved. The synthesis of THL was accomplished in 10 steps and 31% overall yield from an achiral ynone. Key to the success of the approach is the use of a bimetallic [Lewis acid](+)[Co(CO)(4)](−) catalyst for a late-stage regioselective carbonylation of an enantiomerically pure cis-epoxide to a trans-β-lactone. The success of this route to THL and its stereoisomers also demonstrated the practicality of the carbonylation catalyst for complex molecule synthesis as well as its functional group compatibility. |
| format | Online Article Text |
| id | pubmed-4120994 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2014 |
| publisher | American Chemical
Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-41209942015-07-08 Total Synthesis of Tetrahydrolipstatin and Stereoisomers via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic Alcohols Mulzer, Michael Tiegs, Brandon J. Wang, Yanping Coates, Geoffrey W. O’Doherty, George A. J Am Chem Soc [Image: see text] A concise enantioselective synthesis of tetrahydrolipstatin (THL) and seven stereoisomers has been achieved. The synthesis of THL was accomplished in 10 steps and 31% overall yield from an achiral ynone. Key to the success of the approach is the use of a bimetallic [Lewis acid](+)[Co(CO)(4)](−) catalyst for a late-stage regioselective carbonylation of an enantiomerically pure cis-epoxide to a trans-β-lactone. The success of this route to THL and its stereoisomers also demonstrated the practicality of the carbonylation catalyst for complex molecule synthesis as well as its functional group compatibility. American Chemical Society 2014-07-08 2014-07-30 /pmc/articles/PMC4120994/ /pubmed/25004122 http://dx.doi.org/10.1021/ja505639u Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) |
| spellingShingle | Mulzer, Michael Tiegs, Brandon J. Wang, Yanping Coates, Geoffrey W. O’Doherty, George A. Total Synthesis of Tetrahydrolipstatin and Stereoisomers via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic Alcohols |
| title | Total Synthesis
of Tetrahydrolipstatin and Stereoisomers
via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic
Alcohols |
| title_full | Total Synthesis
of Tetrahydrolipstatin and Stereoisomers
via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic
Alcohols |
| title_fullStr | Total Synthesis
of Tetrahydrolipstatin and Stereoisomers
via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic
Alcohols |
| title_full_unstemmed | Total Synthesis
of Tetrahydrolipstatin and Stereoisomers
via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic
Alcohols |
| title_short | Total Synthesis
of Tetrahydrolipstatin and Stereoisomers
via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic
Alcohols |
| title_sort | total synthesis
of tetrahydrolipstatin and stereoisomers
via a highly regio- and diastereoselective carbonylation of epoxyhomoallylic
alcohols |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120994/ https://www.ncbi.nlm.nih.gov/pubmed/25004122 http://dx.doi.org/10.1021/ja505639u |
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