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• W2046240890 endingPage "1933" @default.
• W2046240890 startingPage "1930" @default.
• W2046240890 abstract "The first total synthesis of the dihydrooxepine-containing epidithiodiketopiperazine (ETP) (−)-acetylaranotin (1) is reported. The key steps of the synthesis include an enantioselective azomethine ylide (1,3)-dipolar cycloaddition reaction to set the absolute and relative stereochemistry, a rhodium-catalyzed cycloisomerization/chloride elimination sequence to generate the dihydrooxepine moiety, and a stereoretentive diketopiperazine sulfenylation to install the epidisulfide. This synthesis provides access to (−)-1 in 18 steps from inexpensive, commercially available starting materials. We anticipate that the approach described herein will serve as a general strategy for the synthesis of additional members of the dihydrooxepine ETP family." @default.
• W2046240890 created "2016-06-24" @default.
• W2046240890 creator A5038661637 @default.
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• W2046240890 date "2011-10-28" @default.
• W2046240890 modified "2023-10-03" @default.
• W2046240890 title "Enantioselective Total Synthesis of (−)-Acetylaranotin, a Dihydrooxepine Epidithiodiketopiperazine" @default.
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• W2046240890 doi "https://doi.org/10.1021/ja209354e" @default.
• W2046240890 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/3271125" @default.
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• W2046240890 hasPublicationYear "2011" @default.
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