309947-17-9Relevant articles and documents
A Pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin
Pettit,Lippert III,Herald
, p. 7438 - 7444 (2000)
In an attempt to develop biologically active compounds from the inactive trans isomer (3a) of stilbene 1a, after asymmetric dihydroxylation to optically pure (R,R)-diol 8 the unexpected racemic diphenylacetaldehyde (9) was generated via a Pinacol rearrangement. Several derivatives of diphenylacetaldehyde 9 were synthesized (11-15) and reported. Further reaction of aldehyde 9 during desilylation through autoxidative decarbonylation afforded benzophenone 2b, designated hydroxyphenstatin, a potent antitumor and antimitotic agent. Hydroxyphenstatin showed potent inhibition of the tubulin assembly (IC50 0.82 μM) and exhibited an ED50 of 2.5 μg/mL against the P388 lymphocytic leukemia cell line.
Metal- and O2-Free Oxidative C-C Bond Cleavage of Aromatic Aldehydes
Hu, Guang,Ramakumar, Kinthada,Brenner-Moyer, Stacey E.
, p. 6972 - 6977 (2017/07/17)
An oxidative C-C cleavage of aldehydes requiring neither metals nor O2 was discovered. Homobenzylic aldehydes and α-substituted homobenzylic aldehydes were cleaved to benzylic aldehydes and ketones, respectively, using nitrosobenzene as an oxidant. This reaction is chemoselective for aromatic aldehydes, as an aliphatic aldehyde was unreactive under these conditions, and other reactive functionality such as ketones and free alcohols are tolerated. A mechanism accounting for the fate of the lost carbon is proposed.
