Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades
Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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Elsevier
2017
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| Online Access: | http://hdl.handle.net/1721.1/110431 https://orcid.org/0000-0002-8601-7799 |
| _version_ | 1826207271683620864 |
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| author | Underwood, Brian Saxton Tanuwidjaja, Jessica Ng, SzeSze Jamison, Timothy F |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Underwood, Brian Saxton Tanuwidjaja, Jessica Ng, SzeSze Jamison, Timothy F |
| author_sort | Underwood, Brian Saxton |
| collection | MIT |
| description | Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. |
| first_indexed | 2024-09-23T13:46:44Z |
| format | Article |
| id | mit-1721.1/110431 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T13:46:44Z |
| publishDate | 2017 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | mit-1721.1/1104312022-09-28T16:08:27Z Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades Underwood, Brian Saxton Tanuwidjaja, Jessica Ng, SzeSze Jamison, Timothy F Massachusetts Institute of Technology. Department of Chemistry Underwood, Brian Saxton Tanuwidjaja, Jessica Ng, SzeSze Jamison, Timothy F Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. Elsevier 2017-07-03T18:53:45Z 2017-07-03T18:53:45Z 2013-04 2013-04 Article http://purl.org/eprint/type/JournalArticle 0040-4020 http://hdl.handle.net/1721.1/110431 Underwood, Brian S.; Tanuwidjaja, Jessica; Ng, Sze-Sze and Jamison, Timothy F. "Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades." Tetrahedron 69, 25 (June 2013): 5205-5220 © 2013 Elsevier Ltd https://orcid.org/0000-0002-8601-7799 en_US http://dx.doi.org/10.1016/j.tet.2013.04.041 Tetrahedron Creative Commons Attribution-NonCommercial-NoDerivs License http://creativecommons.org/licenses/by-nc-nd/4.0/ application/pdf Elsevier PMC |
| spellingShingle | Underwood, Brian Saxton Tanuwidjaja, Jessica Ng, SzeSze Jamison, Timothy F Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades |
| title | Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades |
| title_full | Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades |
| title_fullStr | Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades |
| title_full_unstemmed | Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades |
| title_short | Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades |
| title_sort | total syntheses of the squalene derived halogenated polyethers ent dioxepandehydrothyrsiferol and armatol a via bromonium and lewis acid initiated epoxide opening cascades |
| url | http://hdl.handle.net/1721.1/110431 https://orcid.org/0000-0002-8601-7799 |
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