ZWITTERIONIC CATALYST MEDIATED MACROCYCLIZATION AND ITS APPLICATION TO BIOACTIVE MOLECULES SYNTHESES

Abstract

HALOCYCLIZATION IS A POWERFUL METHODOLOGY TO CONSTRUCT A CYCLIC COMPOUND FROM A LINEAR ALKENE SUBSTRATE. THE APPLICATION OF HALOCYCLIZATION TO SYNTHESIZE MEDIUM (7- TO 9-MEMBERED) LACTONES AND LACTAMS IS, HOWEVER, HIGHLY UNCOMMON IN THE LITERATURE. AS THESE CYCLIC STRUCTURES COMMONLY OCCUR IN A VARIETY OF DRUGS AND BIOACTIVE MOLECULES, MILD AND EFFICIENT METHODS TO SYNTHESIZE SUCH COMPOUNDS WOULD BE HIGHLY DESIRABLE IN SYNTHETIC ORGANIC CHEMISTRY. THE WORK IN THIS THESIS SEEKS TO ADDRESS THE CURRENT GAP IN THE LITERATURE BY DETAILING NEWLY DEVELOPED ORGANOCATALYTIC METHODS TO ACCESS SUCH COMPOUNDS VIA HALOCYCLIZATION. THE AREAS OF FOCUS WILL BE ON (1) MEDIUM RING SIZE BROMOLACTONIZATION; (2) BROMOLACTAMIZATION TO GIVE A VARIETY OF LACTAM RING SIZES AND (3) ENANTIOSELECTIVE BROMOLACTAMIZATION. THE RESULTANT PRODUCTS CAN BE OBTAINED IN GOOD YIELDS AND/OR ENANTIOSELECTIVITIES.