Synthesis of modified methyl furanosides by intramolecular oxa-Michael reaction followed by Pummerer rearrangement.
A new method is described for the synthesis of ribofuranoses 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.
Gamba-Sanchez
Diego
D
Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, DCSO, F-91128 Palaiseau, France.
Prunet
Joëlle
J
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011090:Polyenes / Q000138:chemical synthesis; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D012266:Ribose / Q000737:chemistry*; D013454:Sulfoxides / Q000737:chemistry
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D005663:Furans; D011090:Polyenes; D012263:Ribonucleosides; D013454:Sulfoxides; D012266:Ribose