Studies towards the synthesis of viridin, colchicine, and highly diverse polymers with polypeptide-like features

Highly diverse polymers with polypeptide-like features have been synthesized by four component Ugi condensation reactions and ring opening metathesis polymerization. These polymers may serve as chiral catalysts, artificial proteins, metal binding agents or new materials for other applications. The polymers were synthesized in two steps in high overall yield. Molecular weights were relatively high and polydispersities uniform and narrow. Glass transition temperatures were indicative of highly crystalline polymers with a high degree of hydrogen bonding. Polymerization of a diastereomeric mixture of monomers resulted in polymers of much higher molecular weights than polymerization of the individual diastereomers.; Studies toward the synthesis of viridin and viridin analogs have been conducted. Synthetic routes developed have focused on construction of the C9--C10 bond. A Suzuki coupling reaction and Claisen rearrangement have been used to make this key bond. The A-ring of viridin has been connected to the C and D-rings. The key Suzuki coupling has been carried out in high yield. The proposed routes allow for synthetic flexibility in the synthesis of viridin analogs.; Studies toward the synthesis of naturally occurring colchicine, desacetamidocolchicine, and colchicine analogs have been carried out. The synthesis of the B-ring has been investigated by attempts to induce an intramolecular cyclization. A six membered ring intramolecular cyclization has been carried out to form a fused A,B,C ring system. Various attempts to form a seven membered ring failed. A synthetic route employing a [3.2.1] bicyclic system allows for flexibility in the synthesis of the crucial C-ring.