posted on 2020-03-16, 18:04authored byEdith
Rodriguez Venegas, Christine L. Willis
A new strategy is described for the
direct conversion of unsaturated
3,5-dihydroxy-diarylheptanoids to dimeric products assembled on trans-2,8-dioxabicyclo[4.4.0]decane frameworks.
The key atom-economical acid-mediated coupling creates 2 rings and
4 new stereocenters in a single-pot process. Oxygen-18 labeling studies
are in accord with reactions proceeding via a cascade mechanism involving
carbocationic intermediates. This approach enabled the concise total
syntheses of analogues of the natural product blepharocalyxin D in
4 steps from simple starting materials.