Synthesis and biological evaluation of a potent salicylihalamide A lactam analogue
Details
Publication Year 2012-10-28, Volume 10, Issue #40, Page 8147-8153
Journal Title
ORGANIC & BIOMOLECULAR CHEMISTRY
Publication Type
Journal Article
Abstract
The first synthesis of a lactam analogue 3 of salicylihalamide A (1) is reported. A key step in the approach was a photochemical acylation coupling between amine 10 and dioxinone 9 to form the amide 19. Acetylation followed by RCM with Grubbs 1st generation catalyst gave the desired E-lactam 23 (E : Z ratio 87: 13) as the major compound. Conversion of macrolactam 23 into the vinyl iodide 26 followed by Cu catalysed cross coupling with the diene amide 7 gave aza-salicylihalamide analogue 3 in good yield. This compound demonstrated potent activity against several human leukaemia cell lines.
Publisher
ROYAL SOC CHEMISTRY
Keywords
FORMAL TOTAL-SYNTHESIS; V-ATPASE INHIBITORS; VACUOLAR ATPASE; L-RHAMNOSE; D-GLUCOSE; (-)-SALICYLIHALAMIDE-A; METATHESIS; DISCOVERY; AMIDES
WEHI Research Division(s)
Chemical Biology
Rights Notice
© Royal Society of Chemistry 2013


Creation Date: 2012-10-28 12:00:00
Last Modified: 0001-01-01 12:00:00
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