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Synthesis of Methylene Exoglycals Using a Modified Julia Olefination

David Gueyrard*, Rose Haddoub, Amine Salem, Nassib Said Bacar, Peter G. Goekjian

*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.gueyrarduniv-lyon1.fr

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

DOI: 10.1055/s-2005-862364 (free Supporting Information)


Abstract

The use of a two-step coupling-elimination procedure allows successful Julia olefination of sugar-derived lactones to provide exomethylene sugars.

see article for more examples



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

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


Key Words

modified Julia olefination, glycals, tetrahydrofurans, olefination, carbohydrate, alkenes, lactones


ID: J60-Y2017