Organic Letters · 2012 · 71 citations · 27 references
Natural SciencesChemistryNatural Product BiosynthesisOrganic ChemistryBiomimetic SynthesisHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisRetrosynthetic AnalysisAromatic Nucleophilic SubstitutionBiomimetic CyclizationRing-forming Reactions
The polycyclic polyprenylated acylphloroglucinol natural product garcibracteatone has been synthesized in four steps from phloroglucinol, using a strategy based on biosynthetic speculation. The key biomimetic transformation is a cascade of 7-endo-trig and 5-exo-trig radical cyclizations followed by a terminating aromatic substitution reaction.
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Total Synthesis of (±)-Garsubellin A
Akiyoshi Kuramochi, Hiroyuki Usuda, Kenzo Yamatsugu et al. · Journal of the American Chemical Society · 2005 · 158 citations