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Article

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Accepted version

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2014-03-21

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/99053

Access to enantiopure 4-substituted 1,5-aminoalcohols from phenylglycinol-derived δ-lactams: synthesis of Haliclona alkaloiods

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http://dx.doi.org/10.1021/jo5002627

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.

Subject

Síntesi orgànica, Alcaloides, Lactames, Compostos heterocíclics

Subject (English)

Organic synthesis, Alkaloids, Lactams, Heterocyclic compounds

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

Citation

AMAT TUSÓN, Mercedes, et al. Access to enantiopure 4-substituted 1,5-aminoalcohols from phenylglycinol-derived δ-lactams: synthesis of Haliclona alkaloiods. Journal of Organic Chemistry. 2014. Vol. 79, num. 6, pags. 2792-2802. ISSN 0022-3263. [consulted: 11 of August of 2026]. Available at: https://hdl.handle.net/2445/99053

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