Fluorous Mixture Synthesis of Fused-Tricyclic Hydantoins. Use of a Redundant Tagging Strategy on Fluorinated Substrates

Sukhdev Manku and Dennis P. Curran*
Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260
J. Org. Chem., 2005, 70 (11), pp 4470–4473
DOI: 10.1021/jo0502596
Publication Date (Web): May 4, 2005
Copyright © 2005 American Chemical Society

Abstract

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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.

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History

  • Published In Issue May 27, 2005
  • Received February 8, 2005

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