Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin AReportar como inadecuado




Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin A - Descarga este documento en PDF. Documentación en PDF para descargar gratis. Disponible también para leer online.

Department of Drug and Natural Product Synthesis, Faculty of Life Sciences, University of Vienna, Althanstraße 14, A-1090 Vienna, Austria





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Abstract Weinreb amidation of ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylate with aromatic amines provides a significantly improved route to anilide-type key intermediates for the synthesis of the anticancer alkaloid, luotonin A, and new A-ring-modified derivatives thereof. This method has advantages concerning overall yield, brevity, and versatility with regard to the aromatic amine component, even if the latter has less favourable nucleophilicity, solubility and-or stability properties. This is demonstrated by the concise synthesis of a small library of luotonin A analogues, including a novel thiophene isostere of the alkaloid. View Full-Text

Keywords: Weinreb amidation; luotonin A; 4+2 cycloaddition; thiophene Weinreb amidation; luotonin A; 4+2 cycloaddition; thiophene





Autor: Norbert Haider * and Simon Nuß

Fuente: http://mdpi.com/



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