| Abstract
| - In an attempt to develop biologically active compounds from the inactive trans isomer (3a) of stilbene1a, after asymmetric dihydroxylation to optically pure (R,R)-diol 8 the unexpected racemicdiphenylacetaldehyde (9) was generated via a Pinacol rearrangement. Several derivatives ofdiphenylacetaldehyde 9 were synthesized (11−15) and reported. Further reaction of aldehyde 9during desilylation through autoxidative decarbonylation afforded benzophenone 2b, designatedhydroxyphenstatin, a potent antitumor and antimitotic agent. Hydroxyphenstatin showed potentinhibition of the tubulin assembly (IC50 0.82 μM) and exhibited an ED50 of 2.5 μg/mL against theP388 lymphocytic leukemia cell line.
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