Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products
The structural features of polycyclic polyether natural products can, in some cases, be traced to their biosynthetic origin. However in case that are less well understood, only biosynthetic pathways that feature dramatic, yet speculative, epoxide-opening cascades are proposed. We summarize how such...
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| Format: | Article |
| Language: | en_US |
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Wiley Blackwell
2013
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| Online Access: | http://hdl.handle.net/1721.1/82094 https://orcid.org/0000-0002-8601-7799 |
| _version_ | 1826193704256274432 |
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| author | Vilotijevic, Ivan Jamison, Timothy F. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Vilotijevic, Ivan Jamison, Timothy F. |
| author_sort | Vilotijevic, Ivan |
| collection | MIT |
| description | The structural features of polycyclic polyether natural products can, in some cases, be traced to their biosynthetic origin. However in case that are less well understood, only biosynthetic pathways that feature dramatic, yet speculative, epoxide-opening cascades are proposed. We summarize how such epoxide-opening cascade reactions have been used in the synthesis of polycyclic polyethers (see scheme) and related natural products.
The group of polycyclic polyether natural products is of special interest owing to the fascinating structure and biological effects displayed by its members. The latter includes potentially therapeutic antibiotic, antifungal, and anticancer properties, and extreme lethality. The polycyclic structural features of this class of compounds can, in some cases, be traced to their biosynthetic origin, but in others that are less well understood, only to proposed biosynthetic pathways that feature dramatic, yet speculative, epoxide-opening cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of polycyclic polyethers and related natural products. |
| first_indexed | 2024-09-23T09:43:21Z |
| format | Article |
| id | mit-1721.1/82094 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T09:43:21Z |
| publishDate | 2013 |
| publisher | Wiley Blackwell |
| record_format | dspace |
| spelling | mit-1721.1/820942022-09-30T16:26:01Z Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products Vilotijevic, Ivan Jamison, Timothy F. Massachusetts Institute of Technology. Department of Chemistry Vilotijevic, Ivan Jamison, Timothy F. The structural features of polycyclic polyether natural products can, in some cases, be traced to their biosynthetic origin. However in case that are less well understood, only biosynthetic pathways that feature dramatic, yet speculative, epoxide-opening cascades are proposed. We summarize how such epoxide-opening cascade reactions have been used in the synthesis of polycyclic polyethers (see scheme) and related natural products. The group of polycyclic polyether natural products is of special interest owing to the fascinating structure and biological effects displayed by its members. The latter includes potentially therapeutic antibiotic, antifungal, and anticancer properties, and extreme lethality. The polycyclic structural features of this class of compounds can, in some cases, be traced to their biosynthetic origin, but in others that are less well understood, only to proposed biosynthetic pathways that feature dramatic, yet speculative, epoxide-opening cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of polycyclic polyethers and related natural products. 2013-11-13T14:13:50Z 2013-11-13T14:13:50Z 2009-07 2009-02 Article http://purl.org/eprint/type/JournalArticle 14337851 1521-3773 http://hdl.handle.net/1721.1/82094 Vilotijevic, Ivan, and Timothy F. Jamison. “Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products.” Angewandte Chemie International Edition 48, no. 29 (July 6, 2009): 5250-5281. https://orcid.org/0000-0002-8601-7799 en_US http://dx.doi.org/10.1002/anie.200900600 Angewandte Chemie International Edition Creative Commons Attribution-Noncommercial-Share Alike 3.0 http://creativecommons.org/licenses/by-nc-sa/3.0/ application/pdf Wiley Blackwell PMC |
| spellingShingle | Vilotijevic, Ivan Jamison, Timothy F. Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products |
| title | Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products |
| title_full | Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products |
| title_fullStr | Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products |
| title_full_unstemmed | Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products |
| title_short | Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products |
| title_sort | epoxide opening cascades in the synthesis of polycyclic polyether natural products |
| url | http://hdl.handle.net/1721.1/82094 https://orcid.org/0000-0002-8601-7799 |
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