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Article Dans Une Revue Tetrahedron Letters Année : 2014

Short and convenient synthesis of two natural phthalides by a copper(I) catalysed Sonogashira/oxacyclisation copper(I) process

Résumé

Total synthesis of (+/-)-herbaric acid and (+/-)-(4-methoxybenzyl)-5,7-dimethoxyphthalide, two natural phthalide products, was achieved in 8 steps and 5 steps, respectively, starting from commercially available 3,5-dimethoxyaniline. The key step of the sequence included a copper-catalysed tandem cross-coupling and oxacylisation reaction of terminal alkynes and 2-iodobenzok acid derivatives via 5-exo-dig cyclisation with high stereo-, regio- and chemoselectivities. This straightforward method allows the preparation of diverse phthalides, which belong to a group of pharmacologically important compounds.
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hal-02637363 , version 1 (27-05-2020)

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J. Petrignet, Samuel Inack Ngi, Mohamed Abarbri, Jérôme Thibonnet. Short and convenient synthesis of two natural phthalides by a copper(I) catalysed Sonogashira/oxacyclisation copper(I) process. Tetrahedron Letters, 2014, 55 (5), pp.982-984. ⟨10.1016/j.tetlet.2013.12.032⟩. ⟨hal-02637363⟩
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