Chemistry and Biology of the Maltepolides
Organic Molecular Chemistry - Synthesis and Characterisation
Final Report Abstract
As a result of our studies, we developed an efficient synthetic route to advanced building blocks for the protecting-group-free total synthesis of maltepolide E. The resulting sequence of steps is rather short and allows rapid preparation of compounds with variations in the stereochemistry at the desired positions. Due to the presence of the highly labile vinylic epoxide groups in the target molecule, we didn’t succeed so far in the key fragment coupling step and in the assembly of the whole molecule. Nevertheless, we continue our efforts in this project with the aim to solve the olefination reaction problem and to bring the synthesis to the completion. We also prepared several conjugate derivatives of maltepolides and investigated their biological activity. The cytotoxicity of the obtained compounds was found to be comparable to that of natural products, but the absolute value was low for authentic maltepolides and conjugates. Further experiments with purely synthetic compounds may provide more information and clarify the matter.
