Total Synthesis of (±)-Actinophyllic Acid
Open Access
- 21 May 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (24), 7568-7569
- https://doi.org/10.1021/ja803158y
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.Keywords
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