Semi-synthesis of Unnatural Narciclasine Derivatives

Abstract

The generation of new structural derivatives of narciclasine, an Amaryllidaceae alkaloid, has been explored. The strategy applied to the semi-synthesis of these derivatives involves a key enolization step that produces an enol at the C1 position. This material was converted into a triflate to functionalize the C1 position through cross-coupling. Initial triflation attempts resulted in functionalization at C6 instead, and the C6 triflate was successfully coupled with different functionalities. All the novel C6 derivatives were fully deprotected and subjected to evaluation of their biological activity. Experimental and spectral data are provided for all new compounds