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- W2037996876 abstract "Abstract A concise synthetic route is described for the synthesis of gabosine A and N. The key step uses a zinc‐mediated tandem reaction where methyl 5‐deoxy‐5‐iodo‐2,3‐ O ‐isopropylidene‐β‐ D ‐ribofuranoside is fragmented to give an unsaturated aldehyde which is allylated in the same pot with 3‐benzoyloxy‐2‐methylallyl bromide. The functionalized octa‐1,7‐diene, thus obtained, is converted into the six‐membered gabosine skeleton by ring‐closing olefin metathesis. Subsequent protective group manipulations and oxidation gives rise to gabosine N in a total of 8 steps from ribose while the synthesis of gabosine A employs an additional step for inverting a secondary hydroxy group. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)" @default.
- W2037996876 created "2016-06-24" @default.
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- W2037996876 date "2009-01-01" @default.
- W2037996876 modified "2023-10-18" @default.
- W2037996876 title "Synthesis of Gabosine A and N from Ribose by the Use of Ring-Closing Metathesis" @default.
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- W2037996876 doi "https://doi.org/10.1002/ejoc.200800983" @default.
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