Synthesis of 2,5-dihydrofuran-fused quinones from ether-tethered diiododiyne.
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.
Yamamoto
Yoshihiko
Y
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, Ookayama, Meguro-ku, Tokyo 152-8552, Japan. yamamoto@apchem.nagoya-u.ac.jp
Takuma
Ryousuke
R
Hotta
Tomitaka
T
Yamashita
Ken
K
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis*; D011809:Quinones / Q000138:chemical synthesis*; D012428:Ruthenium
D000480:Alkynes; D005663:Furans; D011809:Quinones; D012428:Ruthenium