A Pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin

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

Research output: Contribution to journalArticlepeer-review

46 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

Fingerprint Dive into the research topics of 'A Pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin'. Together they form a unique fingerprint.

Cite this