A pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin.

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 (IC(50) 0.82 microM) and exhibited an ED(50) of 2.5 microg/mL against the P388 lymphocytic leukemia cell line.

• Authors: G R Pettit, J W Lippert 3rd, D L Herald
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 65 Issue 22 Pg. 7438-44 (Nov 03 2000) ISSN: 0022-3263 [Print] United States
• PMID: 11076601 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Antineoplastic Agents
• Benzophenones
• Indicators and Reagents
• hydroxyphenstatin

Topics

• Africa
• Antineoplastic Agents (chemical synthesis)
• Benzophenones (chemical synthesis)
• Crystallography, X-Ray
• Indicators and Reagents
• Molecular Conformation
• Oxidation-Reduction
• Plants, Medicinal (chemistry)