| Ristocetin A belongs to vancomycin family of antibiotics, which are currently our last hope against bacterial infections caused by methicillin-resistant Staphylococcus aureus. We are interested in applying our ruthenium-mediated SNAr reaction protocol to the total synthesis of ristocetin A aglycon. This thesis describes efforts undertaken towards that goal.; Various subunits representing D, E, F and G ring amino acid residues present in the ristocetin A aglycon were synthesized on mulit-gram scale. Sharpless asymmetric aminohydroxylation and Sharpless dihydroxylation were the key reactions used. Also ruthenium metal was installed on various phenylalanines and phenylglycines by simply refluxing the corresponding aromatic compound with [CpRu(CH3CN)3]PF6 in 1,2-dichloroethane. The F-O-G ether linkage was formed by ruthenium-mediated intermolecular S NAr reaction. ABCD system 1.42, which was available for use, was elaborated to the 16-membered macrocycle 3.13 by employing ruthenium-mediated intermolecular SNAr reaction.*; *Please refer to dissertation for diagrams. |
