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

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.

Domains: Organic chemistry

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⟩