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- W2952810396 abstract "Abstract The three-carbon ring expansion methodology commences with the preparation of a cyclic allene (C9, C11, C13), readily available from the corresponding cycloalkene via dibromocarbene addition and subsequent treatment with methyllithium. Dichloroketene addition to the cyclic allene regioselectively provides the [2+2] cycloadduct, which is reductively dechlorinated with zinc in methanol. The resulting cyclobutanone is then catalytically hydrogenated; cyclobutanone ring opening is affected with trimethylsilyl iodide; immediate dehydroiodination of the resulting β-iodocycloalkanone with diazabicycloundecane (DBU) provides the corresponding macrocyclic enone. The 15-membered enone was converted to d , l -muscone with (CH 3 ) 2 CuLi." @default.
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- W2952810396 date "2008-11-11" @default.
- W2952810396 modified "2023-09-22" @default.
- W2952810396 title "ChemInform Abstract: A Three-Carbon (n + 1 + 2) Ring Expansion Method for the Synthesis of Macrocyclic Enones. Application to Muscone Synthesis." @default.
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- W2952810396 doi "https://doi.org/10.1002/chin.200846064" @default.
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