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Pauson-Khand Adducts of N-Boc-propargylamine: A New Approach to 4,5-Disubstituted Cyclopentenones Aiguabella Font, Núria Pesquer, Albert Verdaguer i Espaulella, Xavier Riera i Escalé, Antoni Ciclització (Química) Química biorgànica Compostos orgànics Síntesi orgànica Hormones Efecte de l'estrès sobre les plantes Estrès (Psicologia) Prostaglandines Biomolècules Ring formation (Chemistry) Bioorganic chemistry Organic compounds Organic synthesis Hormones Effect of stress on plants Stress (Psychology) Prostaglandins Biomolecules 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. 2014-02-20T13:16:35Z 2014-05-28T22:02:23Z 2013-05-28 2014-02-20T12:18:26Z info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion 1523-7060 https://hdl.handle.net/2445/50467 632485 eng Versió postprint del document publicat a: http://dx.doi.org/10.1021/ol400999a Organic Letters, 2013, vol. 15, num. 11, p. 2696-2699 http://dx.doi.org/10.1021/ol400999a (c) American Chemical Society , 2013 info:eu-repo/semantics/openAccess 4 p. application/pdf American Chemical Society Articles publicats en revistes (Química Inorgànica i Orgànica)