106566-74-9Relevant academic research and scientific papers
PLANOID DISTORTIONS IN BRIDGED SPIROCOMPOUNDS FORMATION OF (ALL-CIS)-FENESTRANE IN THE ATTEMPTED SYNTHESIS OF THE (CIS,CIS,CIS,TRANS)-ISOMER
Luyten, M.,Keese, R.
, p. 1687 - 1691 (1986)
Molecular distortions in bridged spirononanes and fenestranes are discussed in terms of symmetry deformation coordinates.This analysis reveals that the central, quaternary carbon atom in most of these compounds shows mainly a decrease of the two opposite ring bond angles, whereas the distortions in fenestranes are dominated by an increase of the two opposite bond angles.Dicyclopentadienone 8 serves as the starting material for the preparation of fenestranes.In the key step of the synthesis, the Pd-catalyzed reductive transannular reaction of the enaminonitrile 13 and the ketolactone 17, (all-cis)-fenestrane 6 is formed instead of the (cis,cis,cis,trans)-isomer 7.
