Universitat de Barcelona
2014-02-20T13:16:35Z
2014-05-28T22:02:23Z
2013-05-28
2014-02-20T12:18:26Z
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.
Article
Accepted version
English
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
American Chemical Society
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
