Conversion of cyclic vinyl sulfones to transposed vinyl phosphonates.
Functionalized cyclic vinyl sulfones were directly converted to the "polarity reversed" vinyl phosphonates through an efficient one pot procedure. Ozonolysis of these vinyl sulfones and vinyl phosphonates furnish complementary sets of termini-differentiated ester-aldehydes. This strategy has been applied for preparation of segments needed for the synthesis of Aplyronine A. The scope and limitations of this transformation were defined.
Noshi
Mohammad N
MN
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, USA.
El-awa
Ahmad
A
Torres
Eduardo
E
Fuchs
Philip L
PL
D007783:Lactones / Q000138:chemical synthesis*; D018942:Macrolides; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013450:Sulfones / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D007783:Lactones; D018942:Macrolides; D013450:Sulfones; D014753:Vinyl Compounds; C104057:aplyronine A; D012694:Serine