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2013-05-28

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/50467

Pauson-Khand Adducts of N-Boc-propargylamine: A New Approach to 4,5-Disubstituted Cyclopentenones

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http://dx.doi.org/10.1021/ol400999a

Abstract

A new approach to the synthesis of 4,5-disubstituted cyclopentenones is described. The strategy is based on the Pauson-Khand (PK) reaction of norbornadiene and N-Boc-propargylamine as alkyne with a masked leaving group, which can be eliminated at will. This approach to the synthesis of 4,5-disubstituted cyclopentenones overcomes the problem of using the alkylation to introduce the alpha-side-chain. As an example, prostane 13-epi-12-oxo-phytodienoic acid (13-epi-12-oxo-PDA) methyl ester was synthesized.

Subject

Ciclització (Química), Química biorgànica, Compostos orgànics, Síntesi orgànica, Hormones, Efecte de l'estrès sobre les plantes, Estrès (Psicologia), Prostaglandines, Biomolècules

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Ring formation (Chemistry), Bioorganic chemistry, Organic compounds, Organic synthesis, Hormones, Effect of stress on plants, Stress (Psychology), Prostaglandins, Biomolecules

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Articles publicats en revistes (Química Inorgànica i Orgànica)
Articles publicats en revistes (Institut de Recerca Biomèdica (IRB Barcelona))

Citation

AIGUABELLA FONT, Núria, et al. Pauson-Khand Adducts of N-Boc-propargylamine: A New Approach to 4,5-Disubstituted Cyclopentenones. Organic Letters. 2013. Vol. 15, num. 11, pags. 2696-2699. ISSN 1523-7060. [consulted: 17 of June of 2026]. Available at: https://hdl.handle.net/2445/50467

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