Affordable Access

deepdyve-link
Publisher Website

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

Authors
  • Yamamoto, Yoshihiko
  • Takuma, Ryousuke
  • Hotta, Tomitaka
  • Yamashita, Ken
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Jun 05, 2009
Volume
74
Issue
11
Pages
4324–4328
Identifiers
DOI: 10.1021/jo9005975
PMID: 19402698
Source
Medline
License
Unknown

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.

Report this publication

Statistics

Seen <100 times