Synthesis of the ABC- and D-ring systems of the indole alkaloid ambiguine G.
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.
Chandra
Aroop
A
Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA.
Viswanathan
Rajesh
R
Johnston
Jeffrey N
JN
D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D026121:Indole Alkaloids; C525724:ambiguine G