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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/154828
Formal total synthesis of amphidinolide E
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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.
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BOSCH HEREU, Lluís, et al. Formal total synthesis of amphidinolide E. Journal of Organic Chemistry. 2017. Vol. 82, num. 20, pags. 11021-11034. ISSN 0022-3263. [consulted: 5 of October of 2026]. Available at: https://hdl.handle.net/2445/154828