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

Nicolas Dussart 1 Huu Vinh Trinh 1 David Gueyrard 1
1 CO2GLYCO - Chimie Organique 2-Glycochimie
ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
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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https://hal-udl.archives-ouvertes.fr/hal-02122513
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Submitted on : Tuesday, May 7, 2019 - 1:59:14 PM
Last modification on : Wednesday, July 8, 2020 - 12:43:59 PM

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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, American Chemical Society, 2016, 18 (19), pp.4790-4793. ⟨10.1021/acs.orglett.6b02160⟩. ⟨hal-02122513⟩

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