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Molecules 2012, 17(10), 11363-11378; doi:10.3390/molecules171011363
Article

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

*  and
Received: 21 August 2012; in revised form: 14 September 2012 / Accepted: 18 September 2012 / Published: 25 September 2012
(This article belongs to the Section Metabolites)
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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.
Keywords: Weinreb amidation; luotonin A; [4+2] cycloaddition; thiophene Weinreb amidation; luotonin A; [4+2] cycloaddition; thiophene
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Haider, N.; Nuß, S. Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin A. Molecules 2012, 17, 11363-11378.

AMA Style

Haider N, Nuß S. Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin A. Molecules. 2012; 17(10):11363-11378.

Chicago/Turabian Style

Haider, Norbert; Nuß, Simon. 2012. "Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin A." Molecules 17, no. 10: 11363-11378.



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