Modified Julia Olefination on Anhydrides: Extension and Limitations. Application to the Synthesis of Maculalactone B - Université de Lyon Access content directly
Journal Articles Organic Letters Year : 2016

Modified Julia Olefination on Anhydrides: Extension and Limitations. Application to the Synthesis of Maculalactone B

Abstract

The preparation of exo-enol esters from cyclic anhydrides is reported using a modified Julia olefination. The reaction is highly stereoselective. The Smiles rearrangement can be performed in a one-pot process, giving a straightforward access to exo-enol lactones. Furthermore, the reaction was extended to semistabilized sulfones, and this methodology was applied to the synthesis of maculalactone B.
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hal-02122513 , version 1 (07-05-2019)

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Nicolas Dussart, Huu Vinh Trinh, David Gueyrard. Modified Julia Olefination on Anhydrides: Extension and Limitations. Application to the Synthesis of Maculalactone B. Organic Letters, 2016, 18 (19), pp.4790-4793. ⟨10.1021/acs.orglett.6b02160⟩. ⟨hal-02122513⟩
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