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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.

SUBMITTER: Chandra A

PROVIDER: S-EPMC2617716 | biostudies-literature | 2007 Nov

REPOSITORIES: biostudies-literature

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Synthesis of the ABC- and D-ring systems of the indole alkaloid ambiguine G.

Chandra Aroop A Viswanathan Rajesh R Johnston Jeffrey N JN

Organic letters 20071102 24

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. ...[more]

PMID: 17975918

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