A photoreactive analogue of the immunosuppressant FTY720

  • J Org Chem. 2006 Mar 3;71(5):2200-2. doi: 10.1021/jo0526237.
Chaode Sun  1 ,  Robert Bittman
Affiliations
  • 1. Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.
PMID: 16497020 DOI: 10.1021/jo0526237
Abstract

An azido group was incorporated into the immunomodulatory agent FTY720, accomplishing the first synthesis of a photoactivatable analogue of this ligand (2) in 9 steps from 2-(4-hydroxyphenyl)ethanol and in 34% overall yield. The key steps are formation of a primary amine at a quaternary center of aniline derivative 13 followed by selective diazotization of the arylamine.

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