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; V. Hruby

doi:10.1055/s-1992-26135

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
, V. Hruby

Research output: Contribution to journal › Article › peer-review

46 Scopus citations

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 language	English (US)
Pages (from-to)	458-460
Number of pages	3
Journal	Synthesis
Issue number	5
DOIs	https://doi.org/10.1055/s-1992-26135
State	Published - 1992
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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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.",

author = "K. Verschueren and G. Toth and D. Tourwe and M. Lebl and \{Van Binst\}, G. and V. Hruby",

year = "1992",

doi = "10.1055/s-1992-26135",

language = "English (US)",

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journal = "Synthesis",

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T1 - A facile synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid, a conformationally constrained tyrosine analogue

AU - Verschueren, K.

AU - Toth, G.

AU - Tourwe, D.

AU - Lebl, M.

AU - Van Binst, G.

AU - Hruby, V.

PY - 1992

Y1 - 1992

N2 - 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.

AB - 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.

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UR - https://www.scopus.com/pages/publications/0026550526#tab=citedBy

U2 - 10.1055/s-1992-26135

DO - 10.1055/s-1992-26135

M3 - Article

SN - 0039-7881

SP - 458

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JO - Synthesis

JF - Synthesis

IS - 5

ER -

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

Abstract

ASJC Scopus subject areas

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