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Molbank 2017, 2017(1), M928;

Ethyl (1R*,10S*,12R*,15S*)-4-Hydroxy-2-oxo-15- (2-oxo-1-pyrrolidinyl)-9-oxatetracyclo[,10.03,8]hexadeca-3,5,7,13-tetraene-13-carboxylate

Centro de Investigación Biomédica, Facultad de Ciencias de la Salud Eugenio Espejo, Universidad Tecnológica Equinoccial, Av. Mariscal Sucre y Mariana de Jesús, Quito 170527, Ecuador
Instituto de Química de Recursos Naturales, Universidad de Talca, Av. Lircay s/n, Casilla 747, Talca 3460000, Chile
Authors to whom correspondence should be addressed.
Academic Editor: Norbert Haider
Received: 13 December 2016 / Revised: 11 January 2017 / Accepted: 13 January 2017 / Published: 18 January 2017
(This article belongs to the Section Organic Synthesis)
PDF [1174 KB, uploaded 18 January 2017]


N-Vinylpirrolidinone reacts with (E)-ethyl 5-hydroxy-3-(4-oxo-4H-chromen-3-yl) acrylate (1) through a domino reaction similar to that reported reaction for ethyl vinyl ether. Inverse electron demand Diels–Alder (IEDDA)–elimination-IEDDA generates isomeric tetracycles 5 and 6. The assignment of the relative stereochemistry of the products was made by comparing the proton couplings with those obtained by reaction with ethyl vinyl ether. View Full-Text
Keywords: domino-reaction; inverse electron demand Diels–Alder; N-vinylpyrrolidinone; chromone derivatives domino-reaction; inverse electron demand Diels–Alder; N-vinylpyrrolidinone; chromone derivatives
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Heredia-Moya, J.; Araya-Maturana, R. Ethyl (1R*,10S*,12R*,15S*)-4-Hydroxy-2-oxo-15- (2-oxo-1-pyrrolidinyl)-9-oxatetracyclo[,10.03,8]hexadeca-3,5,7,13-tetraene-13-carboxylate. Molbank 2017, 2017, M928.

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