Total synthesis of (+/-)-actinophyllic acid.
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.
Martin
Connor L
CL
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
Overman
Larry E
LE
Rohde
Jason M
JM
D026121:Indole Alkaloids / Q000138:chemical synthesis*; D008314:Malonates / Q000737:chemistry*; D008722:Methods
D026121:Indole Alkaloids; D008314:Malonates; C500686:actinophyllic acid; C006860:2-n-butylmalonate