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Total synthesis of (+/-)-actinophyllic acid.

ABSTRACT: The first total synthesis of (+/-)-actinophyllic acid (1) is reported. Key steps of this synthesis include an intramolecular oxidative coupling of ketone and malonic ester enolates and an aza-Cope-Mannich rearrangement that assembled the core structure of the natural product's unique ring system. The synthesis was accomplished from di-tert-butyl malonate in 8% overall yield by a concise sequence that proceeds by way of only seven isolated intermediates.

SUBMITTER: Martin CL

PROVIDER: S-EPMC2654095 | biostudies-literature | 2008 Jun

REPOSITORIES: biostudies-literature

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Total synthesis of (+/-)-actinophyllic acid.

Martin Connor L CL Overman Larry E LE Rohde Jason M JM

Journal of the American Chemical Society 20080521 24

The first total synthesis of (+/-)-actinophyllic acid (1) is reported. Key steps of this synthesis include an intramolecular oxidative coupling of ketone and malonic ester enolates and an aza-Cope-Mannich rearrangement that assembled the core structure of the natural product's unique ring system. The synthesis was accomplished from di-tert-butyl malonate in 8% overall yield by a concise sequence that proceeds by way of only seven isolated intermediates. ...[more]

PMID: 18491907

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