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

doi:10.3390/molecules171011363

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

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

Norbert Haider* and Simon Nuß

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

* Author to whom correspondence should be addressed.

Received: 21 August 2012; in revised form: 14 September 2012 / Accepted: 18 September 2012 / Published: 25 September 2012

(This article belongs to the Section Natural Products)

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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

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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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