Synthesis of the ABC framework of tamulamides A and B
Part of special issue: Symposium in Print in honour of Laura Kiessling, Tetrahedron Prize for Creativity in Organic Chemistry 2017.
| Main Authors: | , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
Elsevier BV
2020
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| Online Access: | https://hdl.handle.net/1721.1/125951 |
| _version_ | 1826211254007496704 |
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| author | Kelley, Elizabeth H. (Elizabeth Helen) Jamison, Timothy F |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Kelley, Elizabeth H. (Elizabeth Helen) Jamison, Timothy F |
| author_sort | Kelley, Elizabeth H. (Elizabeth Helen) |
| collection | MIT |
| description | Part of special issue: Symposium in Print in honour of Laura Kiessling, Tetrahedron Prize for Creativity in Organic Chemistry 2017. |
| first_indexed | 2024-09-23T15:03:02Z |
| format | Article |
| id | mit-1721.1/125951 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T15:03:02Z |
| publishDate | 2020 |
| publisher | Elsevier BV |
| record_format | dspace |
| spelling | mit-1721.1/1259512022-10-02T00:17:53Z Synthesis of the ABC framework of tamulamides A and B Kelley, Elizabeth H. (Elizabeth Helen) Jamison, Timothy F Massachusetts Institute of Technology. Department of Chemistry Part of special issue: Symposium in Print in honour of Laura Kiessling, Tetrahedron Prize for Creativity in Organic Chemistry 2017. Synthesis of the fused tetrahydrofuran motif comprising the ABC rings of the marine ladder polyethers tamulamides A and B has been achieved via two different polyepoxide cascade strategies. Investigations into a triepoxide cascade under aqueous conditions revealed the importance of the electronic nature of the cascade end-group with this initial approach. Ultimately, a diepoxide cascade under basic conditions proved most successful, providing the ABC tetrahydropyran triad in 41% yield. NIGMS (grant no. GM72566) 2020-06-23T19:13:16Z 2020-06-23T19:13:16Z 2018-10 2019-12-18T17:49:39Z Article http://purl.org/eprint/type/JournalArticle 0968-0896 https://hdl.handle.net/1721.1/125951 Kelley, Elizabeth H., and Timothy F. Jamison, "Synthesis of the ABC framework of tamulamides A and B." Bioorganic & Medicinal Chemistry 26, 19 (Oct. 2018): 5327-35 doi 10.1016/J.BMC.2018.04.046 ©2018 Author(s) en 10.1016/J.BMC.2018.04.046 Bioorganic & Medicinal Chemistry Creative Commons Attribution-NonCommercial-NoDerivs License http://creativecommons.org/licenses/by-nc-nd/4.0/ application/pdf Elsevier BV PMC |
| spellingShingle | Kelley, Elizabeth H. (Elizabeth Helen) Jamison, Timothy F Synthesis of the ABC framework of tamulamides A and B |
| title | Synthesis of the ABC framework of tamulamides A and B |
| title_full | Synthesis of the ABC framework of tamulamides A and B |
| title_fullStr | Synthesis of the ABC framework of tamulamides A and B |
| title_full_unstemmed | Synthesis of the ABC framework of tamulamides A and B |
| title_short | Synthesis of the ABC framework of tamulamides A and B |
| title_sort | synthesis of the abc framework of tamulamides a and b |
| url | https://hdl.handle.net/1721.1/125951 |
| work_keys_str_mv | AT kelleyelizabethhelizabethhelen synthesisoftheabcframeworkoftamulamidesaandb AT jamisontimothyf synthesisoftheabcframeworkoftamulamidesaandb |