The syntheses of detoxins B1 and B3: The synthesis of 3(S)-pyrrolidinol from L-glutamic acid and synthetic studies toward didemnins A, B, and C

The pyrrolidine nucleus is found in many biologically important natural products. This dissertation deals with the synthesis of several such compounds. In particular, the syntheses of prolyldepsipeptides and 3(S)-pyrrolidinol are discussed. In all cases, readily available amino acids are used as a source of chirality for the target molecules. In the first section, the syntheses of detoxins B$\sb1$ and B$\sb3$ from L-proline are described. These compounds are members of the detoxin complex which is a selective antagonist for the antibiotic blasticidin S. This antibiotic is used in Japan to control several agricultural diseases. In the next section, the synthesis of 3(S)-pyrrolidinol is discussed. In this synthesis, the readily available amino acid L-glutamic acid is converted to the optically pure product using conventional functional group transformations and inexpensive reagents. Finally, efforts toward the syntheses of the macrocyclic depsipeptides didemnins A, B, and C are disclosed. The didemnins exhibit promising antitumor and antiviral activities. They also contain several synthetically challenging substructural features. Among the subunits originally proposed for the structure of the didemnins is the rare amino acid (3S,4R) statine whose synthesis has been accomplished