Frans-Stilbene, synthesis

SYNTHESIS OF SYMMETRICAL frans-STILBENES BY A DOUBLE HECK REACTION OF (ARYLAZO)AMINES WITH VINYLTRIETHOXYSILANE frans-4,4 -DIBROMOSTILBENE... 

G.R. Pettit and co-workers converted a highly substituted frans-stilbene derivative to the strong cancer cell growth inhibitor and antimitotic agent hydroxyphenstatin. The key step of the synthesis was a BFs-OEta-catalyzed pinacol rearrangement of an optically active vicinal diol to afford a substituted diphenylacetaldehyde in racemic form. From this key intermediate, several derivatives were prepared in addition to the target molecule. 

Y. Cbun (2002). Design, synthesis, and discovery of novel frans-stilbene analogues as potent and selective human cytoehrome P450 IBl inhibitors. J. Med. Chem. 45, 160-164. 

The synthesis of thermally stable but EJV-crosslinkable copolyesters derived from PCCD has been recently reported (56). Polycondensation was made using 1,4-CHDM and mixtures of 1,4-dimethylcyclohexane dicarboxylate and dimethyl-frans-4,4 -stilbene dicarboxylate (SD) in variable ratios (Figure 6.13). The incorporation of the photoreactive groups increased the T of the copolyesters, which increased further upon crosslinking, he crosslinking mechanism consisted of a face-to-face dimerization and subsequent [2+2] cycloaddition of the stilbene moieties. 

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