Sequential Ketene Generation from Dioxane-4,6-dione-keto-dioxinones for the Synthesis of Terpenoid Resorcylates

Trapping of the ketene generated from the thermolysis of 2-methyl-2-phenyl-1,3-dioxane-4,6-dione-keto-dioxinone at 50 °C with primary, secondary, or tertiary alcohols gave the corresponding dioxinone β-keto-esters in good yield under neutral conditions. These intermediates were converted by palladiu...

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Bibliographic Details
Published in:Organic letters 2016-04, Vol.18 (8), p.1800-1803
Main Authors: Elliott, Daniel C, Ma, Tsz-Kan, Selmani, Aymane, Cookson, Rosa, Parsons, Philip J, Barrett, Anthony G. M
Format: Article
Language:English
Subjects:
Benzopyrans - chemical synthesis
Benzopyrans - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Catalysis
Chromans - chemical synthesis
Chromans - chemistry
Dioxanes - chemistry
Ethylenes - chemistry
Ketones - chemistry
Molecular Structure
Palladium - chemistry
Stereoisomerism
Terpenes - chemical synthesis
Terpenes - chemistry
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Summary:Trapping of the ketene generated from the thermolysis of 2-methyl-2-phenyl-1,3-dioxane-4,6-dione-keto-dioxinone at 50 °C with primary, secondary, or tertiary alcohols gave the corresponding dioxinone β-keto-esters in good yield under neutral conditions. These intermediates were converted by palladium(0)-catalyzed decarboxylative allyl migration and aromatization into the corresponding β-resorcylates. These transformations were applied to the syntheses of the natural products (±)-cannabiorci­chromenic and (±)-dauri­chromenic acid.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00533