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Open AccessArticle

Multicomponent Domino Reaction in the Asymmetric Synthesis of Cyclopentan[c]pyran Core of Iridoid Natural Products

Dpto. de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain
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Molecules 2020, 25(6), 1308; https://doi.org/10.3390/molecules25061308
Received: 13 February 2020 / Revised: 7 March 2020 / Accepted: 8 March 2020 / Published: 13 March 2020
(This article belongs to the Special Issue Application of Organic Synthesis to Bioactive Compounds)
The asymmetric synthesis of a compound with the cyclopentan[c]pyran core of iridoid natural products in four steps and 40% overall yield is reported. Our methodology includes a one-pot tandem domino reaction which provides a trisubstituted cyclopentane with five new completely determined stereocenters, which were determined through 2D homo and heteronuclear NMR and n.O.e. experiments on different compounds specially designed for this purpose, such as a dioxane obtained from a diol. Due to their pharmaceutical properties, including sedative, analgesic, anti-inflammatory, CNS depressor or anti-conceptive effects, this methodology to produce the abovementioned iridoid derivatives, is an interesting strategy in terms of new drug discovery as well as pharmaceutical development. View Full-Text
Keywords: chiral lithium amide; asymmetric aza-Michael addition; asymmetric domino reaction; multicomponent reaction; cyclopentan[c]pyran; iridoid; nepetalactone chiral lithium amide; asymmetric aza-Michael addition; asymmetric domino reaction; multicomponent reaction; cyclopentan[c]pyran; iridoid; nepetalactone
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Manchado, A.; Ramos, V.E.; Díez, D.; Garrido, N.M. Multicomponent Domino Reaction in the Asymmetric Synthesis of Cyclopentan[c]pyran Core of Iridoid Natural Products. Molecules 2020, 25, 1308.

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