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Total Synthesis of (±)-Actinophyllic Acid
[Image: see text] The first total synthesis of (±)-actinophyllic acid (1) is reported. Key steps of this synthesis include an intramolecular oxidative coupling of ketone and malonic ester enolates and an aza-Cope−Mannich rearrangement that assembled the core structure of the natural product’s unique...
| Autores principales: | , , |
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| Formato: | Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2008
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2654095/ https://www.ncbi.nlm.nih.gov/pubmed/18491907 http://dx.doi.org/10.1021/ja803158y |
| _version_ | 1782165330259345408 |
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| author | Martin, Connor L. Overman, Larry E. Rohde, Jason M. |
| author_facet | Martin, Connor L. Overman, Larry E. Rohde, Jason M. |
| author_sort | Martin, Connor L. |
| collection | PubMed |
| description | [Image: see text] The first total synthesis of (±)-actinophyllic acid (1) is reported. Key steps of this synthesis include an intramolecular oxidative coupling of ketone and malonic ester enolates and an aza-Cope−Mannich rearrangement that assembled the core structure of the natural product’s unique ring system. The synthesis was accomplished from di-tert-butyl malonate in 8% overall yield by a concise sequence that proceeds by way of only seven isolated intermediates. |
| format | Text |
| id | pubmed-2654095 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2008 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-26540952009-03-20 Total Synthesis of (±)-Actinophyllic Acid Martin, Connor L. Overman, Larry E. Rohde, Jason M. J Am Chem Soc [Image: see text] The first total synthesis of (±)-actinophyllic acid (1) is reported. Key steps of this synthesis include an intramolecular oxidative coupling of ketone and malonic ester enolates and an aza-Cope−Mannich rearrangement that assembled the core structure of the natural product’s unique ring system. The synthesis was accomplished from di-tert-butyl malonate in 8% overall yield by a concise sequence that proceeds by way of only seven isolated intermediates. American Chemical Society 2008-05-21 2008-06-18 /pmc/articles/PMC2654095/ /pubmed/18491907 http://dx.doi.org/10.1021/ja803158y Text en Copyright © 2008 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org. 40.75 |
| spellingShingle | Martin, Connor L. Overman, Larry E. Rohde, Jason M. Total Synthesis of (±)-Actinophyllic Acid |
| title | Total Synthesis of (±)-Actinophyllic Acid |
| title_full | Total Synthesis of (±)-Actinophyllic Acid |
| title_fullStr | Total Synthesis of (±)-Actinophyllic Acid |
| title_full_unstemmed | Total Synthesis of (±)-Actinophyllic Acid |
| title_short | Total Synthesis of (±)-Actinophyllic Acid |
| title_sort | total synthesis of (±)-actinophyllic acid |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2654095/ https://www.ncbi.nlm.nih.gov/pubmed/18491907 http://dx.doi.org/10.1021/ja803158y |
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