Double lawton SN2'addition to epoxyvinyl sulfones: selective construction of the stereotetrads of aplyronine A.
[reaction: see text] Enantiopure epoxyvinyl sulfones function as templates for the diastereoselective construction of the three stereotetrads of aplyronine A. Lawton S(N)2' addition of 3,5-dimethylpyrazole followed by its displacement in an alcohol-directed Lawton S(N)2' reaction establishes the required product stereochemistry with high selectivity.
El-Awa
Ahmad
A
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
Fuchs
Philip
P
D004852:Epoxy Compounds / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D004852:Epoxy Compounds; D007783:Lactones; D018942:Macrolides; D013450:Sulfones; D014753:Vinyl Compounds; C104057:aplyronine A; D012694:Serine