Enantioselective syntheses of (+)-xylarenal A and ent-xylarenal A |
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Authors: | Díaz Sandra González Asensio Bradshaw Ben Cuesta Javier Bonjoch Josep |
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Institution: | Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain. |
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Abstract: | reaction: see text] The total synthesis of the sesquiterpenoid xylarenal A is reported. This first synthetic entry to an eremophilane terpenoid with an exocyclic vinyl aldehyde unit involves the use of the bicyclic enone (+)-3, which after a gamma-oxidation and alpha'-allylation leads to the formation of the ketone (+)-8. After its acylation, an oxidative cleavage of the allyl side chain followed by alpha-methylenation of the resulting aldehyde gives (+)-xylarenal A (1). The synthesis of (-)-xylarenal A from (-)-3 is also reported. Moreover, the first total synthesis of the trinoreremophilane (+)-1alpha-hydroxyisoondetianone (5) is described. |
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