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Synthesis of 2,5-dihydrofuran-fused quinones from ether-tethered diiododiyne.

Authors
Type
Published Article
Journal
The Journal of Organic Chemistry
0022-3263
Publisher
American Chemical Society
Publication Date
Volume
74
Issue
11
Pages
4324–4328
Identifiers
DOI: 10.1021/jo9005975
PMID: 19402698
Source
Medline

Abstract

Biologically interesting 2,5-dihydrofuran-fused quinones were synthesized via the ruthenium-catalyzed [2 + 2 + 2] cycloaddition of an ether-tethered diiododiyne with alkynes, copper-catalyzed Ullmann coupling of the resultant fused p-diiodobenzenes with methanol or allyl alcohol, and subsequent oxidation of phenol derivatives. The double Claisen rearrangement of the bis(allyl) ether product furnished a diallylhydroquinone derivative, which underwent iron-catalyzed oxidation, ring-closing metathesis, and dehydrogenation to deliver 1,3-dihydronaphtho[2,3-c]furan-4,9-dione.

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