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Synthesis 1992; 1992(5): 458-460
DOI: 10.1055/s-1992-26135
short paper
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A Facile Synthesis of 1,2,3,4-Tetrahydro-7-hydroxyisoquinoline-3-carboxylic Acid, a Conformationally Constrained Tyrosine Analogue

Kris Verschueren* , Géza Toth, Dirk Tourwé, Michal Lebl, Georges Van Binst, Victor Hruby
  • *Eenheid Organische Chemie, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium
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Publication Date:
17 September 2002 (online)

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A rapid synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid is given. Pictet-Spengler reaction on diiodo- or dibromo-substituted tyrosine (3-(3,5-dihalo-4-hydroxyphenyl)-2-aminopropanoic acid), followed by catalytic dehalogenation gives the desired compound in high optical purity.