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) |
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Pages (from-to) | 7438-7444 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 65 |
Issue number | 22 |
DOIs | |
State | Published - Nov 3 2000 |
ASJC Scopus subject areas
- Organic Chemistry