Total Synthesis of 3-Oxyangeloyl Tremetone

Abstract

Retrosynthetic analysis is a commonly employed methodology in the development of new pharmaceuticals.1 Historically, plants have been used for their medicinal benefits.2 The process of extracting the medicinally active compounds is typically not possible on a large, industrial scale. Therefore, the active compounds’ identities were determined, and those molecules could be synthesized via organic chemistry methodologies. Among the many compounds that have been isolated and identified, compounds containing heterocyclic, aromatic and fused components have been of special interest. The target molecule chosen for this project was originally extracted from a medicinal root from the Chilean Altiplano.3 Through retrosynthetic analysis, the target molecule was broken down into simpler, readily available building blocks and a synthetic pathway was proposed for its formation. The molecule is classified as a tremetone and has shown analgesic activity (painkiller).3 The proposed synthesis to create this molecule contains five, cost effective steps using inexpensive reagents.