Enantiodivergent synthesis of muricatacin related lactones from D-xylose based on the latent symmetry concept: preparation of two novel cytotoxic (+)- and (-)-muricatacin 7-oxa analogs

Enantiodivergent formal synthesis of (+)- and (-)-muricatacins from D-xylose has been accomplished through utilization of the latent plane of symmetry present in the starting monosaccharide. This approach was extended to the preparation of two novel (+)- and (-)-muricatacin 7-oxa analogs (2 and ent-2, respectively), which showed in vitro antitumor activity toward some human malignant cells. The analog ent-2 showed a powerful antiproliferative activity against the K562 cell line, being 36-fold more potent than the standard cytotoxic agent, doxorubicin. Compound 2, however, showed a powerful cytotoxic activity against HL-60 cells, being more than 17-fold more potent with respect to the reference compound. (c) 2006 Elsevier Ltd. All rights reserved.