Next Article in Journal
Study of the in Vitro Antiplasmodial, Antileishmanial and Antitrypanosomal Activities of Medicinal Plants from Saudi Arabia
Previous Article in Journal
A Concise Synthesis of Glycolipids Based on Aspartic Acid Building Blocks
Article Menu

Export Article

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

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

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 / Revised: 14 September 2012 / Accepted: 18 September 2012 / Published: 25 September 2012
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [258 KB, uploaded 18 June 2014]   |  


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

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top