115296-91-8Relevant academic research and scientific papers
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.
