Titel
Weinreb Amidation as the Cornerstone of an Improved Synthetic Route to A-Ring-Modified Derivatives of Luotonin A
Autor*in
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.
Stichwort
Weinreb amidationluotonin A[4+2] cycloadditionthiophene
Objekt-Typ
Sprache
Englisch [eng]
Persistent identifier
Erschienen in
Titel
Molecules
Band
17
Ausgabe
12
Seitenanfang
11363
Seitenende
11378
Publication
MDPI AG
Erscheinungsdatum
2012
Zugänglichkeit
Rechte
Rechteangabe
© 2012 by the authors
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