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Title: Access to enantiopure 4-substituted 1,5-aminoalcohols from phenylglycinol-derived δ-lactams: synthesis of Haliclona alkaloiods
Author: Amat Tusón, Mercedes
Guignard, Guillaume
Llor Brunés, Núria
Bosch Cartes, Joan
Keywords: Síntesi orgànica
Compostos heterocíclics
Organic synthesis
Heterocyclic compounds
Issue Date: 21-Mar-2014
Publisher: American Chemical Society
Abstract: LiNH2BH3-promoted reductive opening of 8-substituted phenylglycinol-derived oxazolopiperidone lactams leads to enantiopure 4-substituted-5-aminopentanols, which are used as starting building blocks in the synthesis of the Haliclona alkaloids haliclorensin C, haliclorensin, and halitulin (formal). The starting lactams are easily accessible by a cyclocondensation reaction of (R)-phenylglycinol with racemic γ-subtituted δ-oxoesters, in a process that involves a dynamic kinetic resolution.
Note: Versió postprint del document publicat a:
It is part of: Journal of Organic Chemistry, 2014, vol. 79, num. 6, p. 2792-2802
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ISSN: 0022-3263
Appears in Collections:Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

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