Synthesis of modified methyl furanosides by intramolecular oxa-Michael reaction followed by Pummerer rearrangement

Gamba-Sanchez, D. and Prunet, J. (2010) Synthesis of modified methyl furanosides by intramolecular oxa-Michael reaction followed by Pummerer rearrangement. Journal of Organic Chemistry, 75(9), pp. 3129-3132. (doi:10.1021/jo100241e)

Gamba-Sanchez, D. and Prunet, J. (2010) Synthesis of modified methyl furanosides by intramolecular oxa-Michael reaction followed by Pummerer rearrangement. Journal of Organic Chemistry, 75(9), pp. 3129-3132. (doi:10.1021/jo100241e)

Full text not currently available from Enlighten.

Abstract

A new method is described for the synthesis of ribo-furanoses modified at the C3 and C5 positions. The key step is an intramolecular oxa-Michael reaction on a vinyl sulfoxide to install the C2 hydroxy group. The methyl furanosides are obtained by Pummerer rearrangement of the sulfoxide into the corresponding aldehyde, acidic deprotection of the benzylidene acetal, and cyclization.

Item Type:Articles
Keywords:ALDEHYDES ANALOGS CONJUGATE ADDITION CYCLOPROPYL DIASTEREOSELECTIVE SYNTHESIS ENANTIOSELECTIVE SYNTHESIS NUCLEOSIDES PROTECTED SYN 1,3-DIOLS SULFOXIDES VINYL SULFONES
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Prunet, Dr Joelle
Authors: Gamba-Sanchez, D., and Prunet, J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
ISSN:0022-3263

University Staff: Request a correction | Enlighten Editors: Update this record