Concise synthesis and transannular inverse electron demand Diels-Alder reaction of [3](3,6)pyridazino[3](1,3)indolophane. Rapid access to a pentacyclic indoloid system.
[reaction: see text] The title compound was synthesized concisely from indole. A 2-fold sequential hydroboration/Suzuki-Miyaura cross-coupling was employed to generate the cyclophane. When heated in N,N-diethylaniline, it underwent a transannular inverse electron demand Diels-Alder (IEDDA) reaction to form a pentacyclic product, which appears to be well suited as a precursor to a variety of indole alkaloids such as strychnine.
Bodwell
Graham J
GJ
Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland, Canada, A1B 3X7. gbodwell@mun.ca
Li
Jiang
J
D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D011083:Polycyclic Compounds / Q000138:chemical synthesis; D011724:Pyridazines / Q000138:chemical synthesis* / Q000737:chemistry
C446686:(3)(3,6)pyridazino(3)(1,3)indolophane; D007202:Indicators and Reagents; D007211:Indoles; D011083:Polycyclic Compounds; D011724:Pyridazines