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: david.gueyrard
univ-lyon1.fr
N. Dussart, H. V. Trinh, D. Gueyrard, Org. Lett., 2016, 18, 4790-4793.
DOI: 10.1021/acs.orglett.6b02160
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Abstract
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.
see article for more examples
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
