| Ristocetin A belongs to the vancomycin group of antibiotics, which are the last line of defense available in the clinic for treating multi-drug resistant bacterial infections and attract considerable interest as a result of their molecular complexity as well as the emergence of vancomycin resistant strains of infectious bacteria. As described in chapter two, construction of a key intermediate of ristocetin A aglycon, the ABCD ring 2.1, was accomplished in the order C-O-D, AB/C-O-D (1–4) and sufficient amounts of this advanced intermediate were prepared for use in completing a total synthesis of the said aglycon. The C-O-D ring system was formed by using the ruthenium-promoted SNAr reaction from a precursor 2.3 already possessing the AB biaryl fragment. At this point, a macrolactamization reaction furnished the ABCD ring system. Atropisomerization was successfully performed for the AB biaryl fragment.; Chapter three provides details of ristocetin A degradation to generate relay intermediates and the conversion of the relay intermediate to the ristocetin A aglycon, which constitutes the final stages of its total synthesis.*; *Please refer to dissertation for diagrams. |
