A facile synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid, a conformationally constrained tyrosine analogue

K. Verschueren, G. Toth, D. Tourwe, M. Lebl, G. Van Binst, Victor J Hruby

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)458-460
Number of pages3
JournalSynthesis
Issue number5
StatePublished - 1992
Externally publishedYes

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Dehalogenation
Carboxylic Acids
Carboxylic acids
Tyrosine
Acids
3-tyrosine
3-hydroxyisoquinoline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A facile synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid, a conformationally constrained tyrosine analogue. / Verschueren, K.; Toth, G.; Tourwe, D.; Lebl, M.; Van Binst, G.; Hruby, Victor J.

In: Synthesis, No. 5, 1992, p. 458-460.

Research output: Contribution to journalArticle

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AU - Van Binst, G.

AU - Hruby, Victor J

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