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

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

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 conce...

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Bibliographic Details
Main Authors: Norbert Haider, Simon Nuß
Format: Article
Language:English
Published: MDPI AG 2012-09-01
Series:Molecules
Subjects:
Weinreb amidation
luotonin A
[4+2] cycloaddition
thiophene
Online Access:http://www.mdpi.com/1420-3049/17/10/11363
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spelling doaj-6ef0bad547344f2c8faddfd6ee6d91142020-11-25T00:29:13ZengMDPI AGMolecules1420-30492012-09-011710113631137810.3390/molecules171011363Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin ANorbert HaiderSimon NußWeinreb 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.http://www.mdpi.com/1420-3049/17/10/11363Weinreb amidationluotonin A[4+2] cycloadditionthiophene
collection DOAJ
language English
format Article
sources DOAJ
author Norbert Haider
Simon Nuß
spellingShingle Norbert Haider
Simon Nuß
Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin A
Molecules
Weinreb amidation
luotonin A
[4+2] cycloaddition
thiophene
author_facet Norbert Haider
Simon Nuß
author_sort Norbert Haider
title Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin A
title_short Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin A
title_full Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin A
title_fullStr Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin A
title_full_unstemmed Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin A
title_sort weinreb amidation as the cornerstone of an improved synthetic route to a-ring-modified derivatives of luotonin a
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2012-09-01
description 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.
topic Weinreb amidation
luotonin A
[4+2] cycloaddition
thiophene
url http://www.mdpi.com/1420-3049/17/10/11363
work_keys_str_mv AT norberthaider weinrebamidationasthecornerstoneofanimprovedsyntheticroutetoaringmodifiedderivativesofluotonina
AT simonnuß weinrebamidationasthecornerstoneofanimprovedsyntheticroutetoaringmodifiedderivativesofluotonina
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