Synthesis and biological evaluation of new jasplakinolide (jaspamide) analogs

Synthesis and biological evaluation of jasplakinolide analogs are described. The synthesis of analogs utilized a diastereoselective syn-aldol reaction and an orthoester Claisen rearrangement as key steps. All synthetic analogs were evaluated for their ability to disrupt the actin cytoskeleton. Compounds 2, 3, and 4 essentially displayed similar activity to jasplakinolide.

Eight new jasplakinolide derivatives were synthesized and evaluated for antitumor activity by measuring their ability to interfere with the actin cytoskeleton. Simplified derivative 4 is essentially as active as natural jasplakinolide.Figure optionsDownload as PowerPoint slide