Transannular Diels-Alder reaction studies with an activated dienophile. An enantioselective synthesis of an A.B.C.[6.6.6.] trans-syn-cis tricycle

Article abstract of DOI:10.1016/S0040-4020(97)00997-6

The synthesis and transannular Diels-Alder reaction of a chiral 14 membered trans-cis-cis (TCC) macrocyclic triene with an activated dienophile leading to an A.B.C.[6.6.6.] tricyclic compound are described. The outcome of the TADA reaction under thermal and catalyzed conditions is discussed.