Suchergebnisse

7 páginas, 1 figura, 7 esquemas, 1 tabla.-- El PDF es la versión post-print. ; The concept of molecular simplification as a drug design strategy to shorten synthetic routes, while keeping or enhancing the biological activity of the lead drug, has been applied to (+)-muconin, an acetogenin with remarkable cytotoxicity. A novel approach that enables the stereoselective synthesis of such a natural compound or its enantiomer from a common precursor is described. An additional advantage of the method is complete stereochemical control and the decrease in the number of chemical steps required, thus providing an enhancement of the overall yield. Antiproliferative studies against the human solid tumor cell lines showed that the aliphatic chain-THF/THP fragment of (+)-muconin has modest cytotoxic activity. The strategy opens the way to preparing novel bioactive acetogenin analogues by shorter synthetic routes. ; The authors thank the MYCT (PPQ2002- 04361-C04-02) of Spain and the Canary Islands Government for supporting this research. F.R.P.C. thanks CajaCanarias for a FPI fellowship. R.C. thanks the Spanish MEC for a FPU fellowship. J.M.P. thanks ICIC for a postdoctoral fellowship. ; Peer reviewed