Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 45, Pages 16096-16099Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b10053
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- SNF [163151]
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The first enantioselective total synthesis of the complex-tricarbocydic sesquiterpenoid periconianone A based on a postulated biogenesis is reported. Key elements of the synthetic route include the use of an isopropenyl group as a removable directing group for stereoselective synthesis, a sequence featuring a Rh-mediated O-H insertion/[3,3]-sigmatropic rearrangement and subsequent alpha-ketol rearrangement, and a late stage aldol reaction to furnish the complex cage-like framework.
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