Multicomponent reactions in organic synthesis: An approach to viridin and viridin analogs

The use of the Passerini (3CC) and Ugi (4CC) reactions to construct novel analogs of the viridin family of furanosteroids and the synthesis of monomers for use in ring opening metathesis polymerization (ROMP) reactions was examined.; A strategy for the synthesis of viridin and wortmannin analogs was investigated that would maintain a high degree of synthetic flexibility while allowing for quick and efficient synthesis of a large number of analogs. The synthesis of highly functionalized oxabicyclo[2.2.1]heptadiene derivatives through the sequential use of an Ugi or Passerini multi-component coupling reaction was examined. The multicomponent reaction allowed for the quick assembly of a large number of structurally diverse products that were subjected to an intramolecular acetylene/furan Diels-Alder reaction. This tandem reaction provided derivatives that can be further functionalized to give analogs of potent PI-3K inhibitors viridin and wortmannin.; The combined application of multicomponent coupling reactions and olefin metathesis chemistry for the preparation of new chemical entities with application as novel biomaterials was also investigated. The compatibility of these two complexity-building reactions made them ideal for the use in generation of novel monomer and polymeric structures. The peptide-like functionality of the resulting monomers may allow for metal binding with application as metal scavenging agents or macromolecular ligands for asymmetric synthesis.