Efforts toward the synthesis of a C3-symmetric triol macrolide and efforts toward the synthesis of a C3-symmetric triacetate triol macrotriamide

Scaffolds are important in biological systems as well as in the study of those systems. The Burke group has generated a number of spatially well-defined C3-symmetric macrocycles. One in particular, 2.18, has been used as a scaffold to display other subunits in two biological systems. This thesis describes efforts toward the synthesis of two different scaffolds, which we hoped could used to study biological systems. Chapter 4 describes efforts to synthesize an analog of 2.18 that offers improved spacing for other applications. Efforts on two distinct routes to a monomer subunit are described.;Like many viruses, HIV, the virus that causes AIDS, utilizes its own proteins in addition to the host cell's native machinery to replicate. Uniquely, HIV infects helper T-cells, which are critical in immune response. Thus, infection of helper T-cells by HIV weakens immune response, making those infected with HIV more vulnerable to attack by other organisms. A number of viral enzymes necessary for the replication of HIV have been targeted in the treatment of the infection. Of recent particular interest are the proteins involved in the entry of HIV into new helper T-cell hosts. gp41, an HIV glycoprotein is critical to this process. Chapter 3 of this thesis describes efforts to synthesize a C3-symmetric scaffold to study this viral entry process and gp41's role in viral fusion. The synthetic route centers around a palladium mediated cycloetherification to form a tetrahydropyran.