Advances in the stereoselective synthesis of antifungal agents and ...

Chapter 7 1527 Summary:Numerous drugs are chiral, generally only one enantiomer istherapeutically active while the other antipode is completely inactive orshows often undesired and/or toxic side effects. For this reason, all newchiral drugs are now formulated in enantiopure form, and consequentlythe synthesis of enantiomerically pure compounds is becoming one of themost important areas in the organic chemistry.Non-steroidal anticancer and antifungal drugs are particularlyinteresting as therapeutic agents. Several classes of these two differentfamilies of drugs contain the same chemical structure e.g. Bifonazole 6aand non-steroidal aromatase inhibitors such as the Menarini anticancerdrug 18 (Fig.7.1).NONRNBifonazole 6a Menarini anticancer Drug 18Fig 7.1: Bifonazole 6a and the Menarini anticancer drug 18.They are characterized by the presence of an N-imidazole group in abenzhydrilic position. The carbon atom link to the three aromatic moietiesis the only chiral centre of the molecule. The present work was aimed atnew procedures for the synthesis of both Bifonazole 6a and the Menariniaromatase inhibitors 18 in enantiomeric form as well as structuralanalogues.In order to prepare enantiopure synthons and final products severalsynthetic methods were developed.A special attention was dedicated to the synthesis of enantiopurebenzhydrols 27a-f and aryl-2-benzo[b]furancarbinols 27g-i and 63a-d.N