A Pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin

George Pettit, J. W. Lippert, D. L. Herald

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51 Scopus citations


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.

Original languageEnglish (US)
Pages (from-to)7438-7444
Number of pages7
JournalJournal of Organic Chemistry
Issue number22
StatePublished - Nov 3 2000

ASJC Scopus subject areas

  • Organic Chemistry


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