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

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-c...

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Bibliographic Details
Published inTetrahedron letters Vol. 55; no. 5; pp. 982 - 984
Main Authors Petrignet, Julien, Inack Ngi, Samuel, Abarbri, Mohamed, Thibonnet, Jérôme
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.01.2014
Elsevier
Subjects
Alkynes
Chemistry
Chemistry, Organic
Copper catalysis
Cross coupling
Cyclisation
Derivatives
Life Sciences
Phthalides
Physical Sciences
Science & Technology
Synthesis (chemistry)
Terminals
Tetrahedrons
Total synthesis
Phthalides
Cyclisation
Copper catalysis
Total synthesis
GAMMA
ROUTE
ACID
ISOCOUMARINS
DERIVATIVES
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Summary: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-iodobenzoïc 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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.12.032