A Pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin

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

doi:10.1021/jo000705j

A Pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin

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

CLAS-NS: Molecular Sciences, School of (SMS)

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	7438-7444
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	65
Issue number	22
DOIs	https://doi.org/10.1021/jo000705j
State	Published - Nov 3 2000

ASJC Scopus subject areas

Organic Chemistry

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title = "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 (IC50 0.82 μM) and exhibited an ED50 of 2.5 μg/mL against the P388 lymphocytic leukemia cell line.",

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T1 - A Pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin

AU - Pettit, George

AU - Lippert, J. W.

AU - Herald, D. L.

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N2 - 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.

AB - 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.

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A Pinacol rearrangement/oxidation synthetic route to hydroxyphenstatin

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