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.
Aroop Chandra, Rajesh Viswanathan, Jeffrey N Johnston. Synthesis of the ABC- and D-ring systems of the indole alkaloid ambiguine G. Organic letters. 2007 Nov 22;9(24):5027-9
PMID: 17975918
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