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- W2469189146 abstract "The levorotatory enantiomers of gabosines D and E were synthesized through a divergent approach that could equally well be applied to the synthesis of the dextrorotatory enantiomers, which have been isolated from natural sources. The approach relies on an initial desymmetrization of p ‐methoxyphenol, followed by an enzymatic resolution that separately provides the two enantiomers of synthon 3 . This versatile synthon can be further transformed into the diverse polyoxygenated cyclohexane target molecules. Key steps in the synthesis of (–)‐gabosines D and E from (4 R ,6 S )‐ 3 are the stereoselective hydroxymethylation at the α‐carbonyl position leading to (+)‐ 4 , and the subsequent reagent‐controlled epoxidation of the carbon–carbon double bond. A branching in the sequence also allowed the synthesis of the anhydrogabosines (–)‐epiepoxydon and (+)‐phyllostine." @default.
- W2469189146 created "2016-07-22" @default.
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- W2469189146 date "2016-07-01" @default.
- W2469189146 modified "2023-10-18" @default.
- W2469189146 title "Filling Some Blanks in a Divergent Approach to Gabosines: Enantioselective Synthesis of (–)‐Epiepoxydon, (+)‐Phyllostine, (–)‐Gabosine D, and (–)‐Gabosine E" @default.
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- W2469189146 doi "https://doi.org/10.1002/ejoc.201600492" @default.
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