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https://hdl.handle.net/2445/154828| Title: | Formal total synthesis of amphidinolide E |
| Author: | Bosch Hereu, Lluís Mola Solà, Laura Petit Roig, Elena Saladrigas, Mar Esteban Jarne, Jordi Costa i Arnau, Anna M. Vilarrasa i Llorens, Jaume |
| Keywords: | Síntesi orgànica Enllaços químics Organic synthesis Chemical bonds |
| Issue Date: | 20-Oct-2017 |
| Publisher: | American Chemical Society |
| Abstract: | A formal total synthesis of the cytotoxic macrolide amphidinolide E is reported. The strategic steps are three Julia-Kocienski reactions (J-K), for the formation of the C5-C6, C9-C10, and C17-C18 double bonds, a Suzuki-Molander C21-C22 bond formation reaction, and a Kita-Trost macrolactonization. The 'instability' of the two dienic systems and of the stereocenter at C2 (allylic methine, alpha to the carboxy group) and the protecting groups at C17-OH and C18-OH have posed difficult challenges. Each Julia-Kocienski olefination has been systematically optimized to provide the highest possible E/Z ratios. |
| Note: | Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.7b01973 |
| It is part of: | Journal of Organic Chemistry, 2017, vol. 82, num. 20, p. 11021-11034 |
| URI: | https://hdl.handle.net/2445/154828 |
| Related resource: | https://doi.org/10.1021/acs.joc.7b01973 |
| ISSN: | 0022-3263 |
| Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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| 677636.pdf | 988.75 kB | Adobe PDF | View/Open |
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