Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 20, Pages 11021-11034Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01973
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Funding
- Spanish Government, FEDER [CTQ2006-15393, CTQ2009-13590, CTQ2012-39230, CTQ2015-71506-R]
- AGAUR, Barcelona [2009SGR825]
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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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