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• W1993764456 abstract "1,4-Disubstituted 2,3-dioxabicyclo[2.2.2]oct-5-enes were dihydroxylated with osmium tetroxide to yield diols anti to the peroxide linkage in a highly selective manner. Reduction of the peroxide bond furnished cyclohexane-1,2,3,4-tetraols with toxocarol relative stereochemistry in excellent yield. This new methodology was employed to synthesize the natural product (1S,2R,3S,4R,5R)-2-methyl-5-(propan-2-yl)cyclohexane-1,2,3,4-tetrol (1) in a short sequence from (R)-alpha-phellandrene. Moreover, during the study of the chemistry of 2,3-dioxabicyclo[2.2.2]octane-5,6-diols a hitherto unknown rearrangement was discovered which has wide applicability for the synthesis of 1,4-dicarbonyls, including optically enriched synthons. A broad range of mechanistic investigations applicable to this rearrangement are also reported." @default.
• W1993764456 created "2016-06-24" @default.
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• W1993764456 date "2008-11-26" @default.
• W1993764456 modified "2023-10-09" @default.
• W1993764456 title "Synthesis and Chemistry of 2,3-Dioxabicyclo[2.2.2]octane-5,6-diols" @default.
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• W1993764456 doi "https://doi.org/10.1021/jo8020506" @default.
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