A Pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin

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

Research output: Contribution to journalArticle

44 Scopus citations

Abstract

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
Volume65
Issue number22
DOIs
StatePublished - Nov 3 2000

ASJC Scopus subject areas

  • Organic Chemistry

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