Synthetic Methods Towards the Core Tricyclic Ring System of Pradimicin A.

摘要

The pradimicins are natural products that are both structurally intriguing to a synthetic chemist and possess biological activity as antifungal and antiviral agents. Our interest towards designing a synthetic route for these compounds and various analogues was sparked by the potential to produce a library of efficient carbohydrate receptors. The initial synthetic approach towards pradimicin A involved a model study of the synthesis of the core tricyclic ring system. This route featured an alkoxyallylboration, ring closing enyne metathesis and Diels-Alder cycloaddition. Chapter 2 describes the efforts towards synthesizing starting materials and the enyne metathesis precursor, which includes a mono-protected trans-diol. Chapter 3 focuses on the reaction conditions and various substrates that were tested for the ring closing enyne metathesis reaction. The optimal route found for the synthesis of the tricyclic ring system featured a one-pot palladium catalyzed cycloisomerization, Diels-Alder reaction and aromatization.