title: Synthesis of the ABC- and D-ring systems of the indole alkaloid ambiguine G.
abstract: A glycine Schiff base Michael addition is used in sequence with free radical-mediated aryl amination to ultimately arrive at the ambiguine G ABC-tricycle convergently. Additionally, thermal Diels-Alder cycloaddition of beta-chloromethacrolein with Cohen's diene is used to diastereoselectively construct the D-cyclohexane ring bearing a neopentyl chloride.
authors.affiliation: Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA.
authors.forename: Aroop
authors.initials: A
authors.lastname: Chandra
authors.forename: Rajesh
authors.initials: R
authors.lastname: Viswanathan
authors.forename: Jeffrey N
authors.initials: JN
authors.lastname: Johnston
mesh_terms: D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C525724:ambiguine G