Fluorous mixture synthesis of fused-tricyclic hydantoins. Use of a redundant tagging strategy on fluorinated substrates.
Simple HPLC experiments were used to identify a redundant tagging scheme wherein six different amino acids were tagged with only four fluorous tags. The tagged amino acids were converted to regiosiomeric mixtures of tricyclic hydantoins. Despite the lack of selectivity, the mixtures were demixed and detagged to give 11 individual pure products in just 25 steps.
Manku
Sukhdev
S
Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260, USA.
Curran
Dennis P
DP
D000596:Amino Acids / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods; D002851:Chromatography, High Pressure Liquid; D006827:Hydantoins / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000596:Amino Acids; D006827:Hydantoins; D006845:Hydrocarbons, Fluorinated