title: Complexity-enhancing acid-promoted rearrangement of tricyclic products of tandem Ugi 4CC/intramolecular Diels-Alder reaction.
abstract: The unexpected rearrangement of 2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1-one products of the tandem Ugi 4CC/intramolecular Diels-Alder reaction in 85% H3PO4 was discovered to provide diastereomerically pure tricyclic bislactam lactone-containing natural product-like products in high yield. Mechanistic rationale for the observed rearrangement was proposed and has been tentatively confirmed by additional experiments.
authors.affiliation: Chemical Diversity Research Institute, Khimki, Moscow Reg., 114401 Russia.
authors.forename: Alexei
authors.initials: A
authors.lastname: Ilyin
authors.forename: Volodymyr
authors.initials: V
authors.lastname: Kysil
authors.forename: Mikhail
authors.initials: M
authors.lastname: Krasavin
authors.forename: Irina
authors.initials: I
authors.lastname: Kurashvili
authors.forename: Alexandre V
authors.initials: AV
authors.lastname: Ivachtchenko