Pharmaceutical Chemistry

Functionalyzed heterocycles are important structures present in several bioactive natural and unnatural products with medicinal and pharmaceutical properties. For instance, many natural oxocanes such as Laurencin, laurenyne or cis-dihydrorhodophytin, which are secondary metabolites isolated from the red algae genus Laurencia exhibit antimicrobial, insecticidal or cytotoxic activities. The corresponding 7-membered oxacycles occur in a great number of mono- and poliethers (such as raspacionin, 3-epi-sodwanone K 3-acetate, or Hemibrevetoxin B) and exhibit important cytotoxic activity. Similarly, examples of azepanes with medicinal properties are the natural Balanol, fungal metabolite isolated from Verticillium balanolides which is a potent PKC inhibitor, ophiocordin, an antibiotic extracted from cultures of Cordyceps ophioglossoides which exhibit antifungal activity or the unnatural (3R,4R,6S)-trihydroxyazepane, which has shown to be a potent inhibitor against R-mannosidase  and R-fucosidase. Following our interest in the synthesis of carbo and heterocycles using silicon-containing substrates, we now present an approach towards the synthesis of different sized oxacycles and nitrogen heterocycles with potential pharmacological properties based in the intramolecular Prins reaction.