112698-71-2Relevant academic research and scientific papers
SULFONE MEDIATED SYNTHESIS OF CYCLOPENTADIENONE EPOXIDES FROM 10-OXATRICYCLO /5.2.1.02,6/ DECADIENONES . A CONVENIENT ROUTE TO epi-PENTENOMYCINS
Klunder, A. J. H.,Houwen-Claassen, A. A. M.,Kooy, M. G.,Zwanenburg, B.
, p. 1329 - 1332 (1987)
Sulfonylmethylation of 10-oxatricyclodecadienone 6 leads to sulfone 4 which forms the key intermediate in the synthesis of 5-alkoxymethylcyclopentadienone epoxides 5.Acid catalyzed hydrolysis of 5 followed by acylation affords epi-pentenomycin derivates 1
SYNTHESIS OF 4- AND 5-SUBSTITUTED 10-OXATRICYCLO2,16>DECADIENONES. FUNCTIONALIZATION OF THE CYCLO-ADDUCT OF FURAN AND CYCLOPENTEN-1,4-DIONE.
Houwen-Claassen, Adrie A. M.,Klunder, A. J. H.,Kooy, M. G.,Steffan, J.,Zwanenburg, B.
, p. 7109 - 7133 (2007/10/02)
Tosylmethylation of the furan derived cyclo-adduct of cyclopentene-1,4-dione, followed by O-ethylation, leads to 5-ethoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo2.6>dien-3-one 14.This sulpone undergoes a smooth displacement of the tosyl group by an ether or thioether function when treated with alcoholates or thiolates.This displacement involves two sonsecutive SN2' substitutions, taking place stereospecifically at the least hindered exo-face of the substrate molecule, i. e. anti to the oxa-bridge.Subsequent reduction with DIBAL or reaction with MeLi provides 4- and/or 5-substituted 10-oxatricyclo2.6>decadienones.
