Sequential Ketene Generation from Dioxane-4,6-dione-keto-dioxinones for the Synthesis of Terpenoid Resorcylates
File(s)
Accepted version
Author(s)
Type
Journal Article
Abstract
Trapping of the ketene generated from the thermolysis of 2-methyl-2-phenyl-1,3-dioxane-4,6-dione-ketodioxinone
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.
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.
Date Issued
2016-04-04
Date Acceptance
2016-04-04
Citation
Organic Letters, 2016, 18 (8), pp.1800-1803
ISSN
1523-7060
Publisher
American Chemical Society
Start Page
1800
End Page
1803
Journal / Book Title
Organic Letters
Volume
18
Issue
8
Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://dx.doi.org/10.1021/acs.orglett.6b00533
Sponsor
Commission of the European Communities
Grant Number
267281
Subjects
Organic Chemistry
03 Chemical Sciences
Publication Status
Published