Synthesis of jaspaquinol and effect on viability of normal and malignant bladder epithelial cell lines.
The synthesis of jaspaquinol 1, a monocyclic diterpene-benzenoid, is reported. Two synthetic routes to this natural product have been developed. The first, utilises a difunctional terpene derivative containing different leaving groups, facilitating the selective introduction of the cyclohexenyl and benzenoid fragments. The alternative route employs a regiospecific Stille cross-coupling reaction to introduce the cyclohexenyl fragment, which occurs without allylic transposition. Preliminary data shows the cell viability of 1 against normal and malignant human bladder epithelial cell lines.
Demotie
Alexandre
A
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
Fairlamb
Ian J S
IJ
Lu
Feng-Ju
FJ
Shaw
Nicola J
NJ
Spencer
Peter A
PA
Southgate
Jennifer
J
D001554:Benzene; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004224:Diterpenes / Q000138:chemical synthesis* / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004847:Epithelial Cells / Q000187:drug effects* / Q000473:pathology; D006801:Humans; D013329:Structure-Activity Relationship; D001743:Urinary Bladder / Q000166:cytology; D001749:Urinary Bladder Neoplasms / Q000188:drug therapy*
D004224:Diterpenes; C494670:jaspaquinol; D001554:Benzene