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oai:recercat.cat:2445/1548282025-12-04T21:41:49Zcom_2072_1057col_2072_478917col_2072_478933

Formal total synthesis of amphidinolide E Bosch Hereu, Lluís Mola Solà, Laura Petit Roig, Elena Saladrigas, Mar Esteban Jarne, Jordi Costa i Arnau, Anna M. Vilarrasa i Llorens, Jaume Síntesi orgànica Enllaços químics Organic synthesis Chemical bonds 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. 2020-04-02T09:43:13Z 2020-04-02T09:43:13Z 2017-10-20 2020-04-02T09:43:13Z info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion 0022-3263 https://hdl.handle.net/2445/154828 677636 eng Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.7b01973 Journal of Organic Chemistry, 2017, vol. 82, num. 20, p. 11021-11034 https://doi.org/10.1021/acs.joc.7b01973 (c) American Chemical Society , 2017 info:eu-repo/semantics/openAccess 14 p. application/pdf American Chemical Society Articles publicats en revistes (Química Inorgànica i Orgànica)