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

Martin CL, Overman LE, Rohde JM - J. Am. Chem. Soc. (2008)

Bottom Line: 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.

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Affiliation: Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.

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.

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

Martin CL, Overman LE, Rohde JM - J. Am. Chem. Soc. (2008)

© Copyright Policy - open-access - ccc-price
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2654095&req=5

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.

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.

Show MeSH