Synthesis of 1,4-naphthoquinone methides via acid-catalyzed cascade cyclizations of benzannulated enediynyl alcohols.
Treatment of benzannulated enediynyl alcohols with trifluoroacetic acid at room temperature promoted a cascade sequence of cyclization reactions, leading to 1,4-naphthoquinone methides. The transformation involved an unusual two-carbon ring expansion from the cyclic alcohols and the construction of the p-quinone methide ring from an acyclic system along the reaction pathway.
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, United States.
Bo
B
Wen
Jeffrey L
JL
Petersen
Kung K
KK
Wang
D000143:Acids / Q000737:chemistry*; D000438:Alcohols / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D053281:Enediynes / Q000737:chemistry*; D045563:Indolequinones / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry*
D000143:Acids; D000438:Alcohols; D053281:Enediynes; D045563:Indolequinones; D009285:Naphthoquinones; C068040:quinone methide; D001554:Benzene; C035342:1,4-naphthoquinone