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

Connor L Martin, Larry E Overman, Jason M Rohde

Index: J. Am. Chem. Soc. 130(24) , 7568-9, (2008)

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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.