Cycloadditions of isobenzofuran to a constrained template bearing neighboring dienophiles.
A high yielding synthesis of the pentacyclic diene-dione 1 has enabled investigation of its reactivity as a double dienophile in Diels-Alder [4+2] cycloadditions with isobenzofuran, leading to novel and highly symmetrical three-sided cavitands 3 and 4.
Stoermer
Martin J
MJ
Centre for Drug Design and Development, Institute for Molecular Bioscience, Gehrmann Laboratories, Research Road, St.Lucia 4072, Queensland, Australia.
Butler
Douglas N
DN
Warrener
Ronald N
RN
Weerasuria
K D V
KD
Fairlie
David P
DP
D001572:Benzofurans / Q000138:chemical synthesis*; D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction
D001572:Benzofurans; D007202:Indicators and Reagents