Total Synthesis of (-)-Maximiscin.
Total Synthesis of (-)-Maximiscin.
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DOI:
10.1021/jacs.0c03202
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发表时间:
2020-05-13
影响因子:
15
通讯作者:
Baran PS
中科院分区:
文献类型:
--
作者:
McClymont KS;Wang FY;Minakar A;Baran PS
A short, enantioselective synthesis of (–)-maximiscin, a structurally-intriguing metabolite of mixed biosynthetic origin, is reported. A retrosynthetic analysis predicated on maximizing ideality and efficiency led to several unusual disconnections and tactics. Formation of the central highly-oxidized pyridone ring through a convergent coupling at the end of the synthesis simplified the route considerably. The requisite building blocks could be prepared from feedstock materials (derived from shikimate and mesitylene). Strategies rooted in hidden symmetry recognition, C–H functionalization, and radical retrosynthesis played key roles developing this concise route.
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