Synthesis and cycloaromatization of a cyclic enyne-allene prodrug.
A simple and stable cyclic enediynone (4) has been synthesized using an intramolecular Nozaki-Hiyama-Kishi cyclization as the key step. Reaction with a thiolate nucleophile led to rapid cycloaromatization of 4. Trapping experiments using 1,4-cyclohexadiene support the intermediacy of an aromatic diradical in the cycloaromatization.
Bekele
Tefsit
T
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907-1392, USA.
Brunette
Steven R
SR
Lipton
Mark A
MA
D000466:Alkadienes / Q000138:chemical synthesis*; D003500:Cyclization; D003510:Cyclohexanes / Q000737:chemistry; D053138:Cyclohexenes; D053281:Enediynes; D008956:Models, Chemical; D011355:Prodrugs / Q000138:chemical synthesis*; D011743:Pyrimidines / Q000138:chemical synthesis*; D013873:Thionucleotides / Q000737:chemistry
D000466:Alkadienes; D003510:Cyclohexanes; D053138:Cyclohexenes; D053281:Enediynes; D011355:Prodrugs; D011743:Pyrimidines; D013873:Thionucleotides; C418567:enediynone; C048401:1,4-cyclohexadiene; C025947:propadiene