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

Nicolas Dussart, Huu Vinh Trinh and David Gueyrard*

*Université de Lyon, ICBMS, UMR 5246 - CNRS, Bat. 308 - Curien (CPE Lyon), Université Claude Bernard Lyon 1, 43 Bd du 11 Novembre 1918, F-69622 Villeurbanne, France, Email:

N. Dussart, H. V. Trinh, D. Gueyrard, Org. Lett., 2016, 18, 4790-4793.

DOI: 10.1021/acs.orglett.6b02160 (free Supporting Information)

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A modified Julia olefination enables a highly stereoselective synthesis of exo-enol esters from cyclic anhydrides. A subsequent one-pot Smiles rearrangement gives a straightforward access to exo-enol lactones. Furthermore, the reaction was extended to semistabilized sulfones and applied to the synthesis of maculalactone B.

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Synthesis of Methylene Exoglycals Using a Modified Julia Olefination

D. Gueyrard, R. Haddoub, A. Salem, N. S. Bacar, P. G. Goekjian, Synlett, 2006, 17, 520-522.

Key Words

modified Julia olefination, phthalides

ID: J54-Y2016