A FACILE SYNTHESIS OF 1,2,3,4-TETRAHYDRO-7-HYDROXYISOQUINOLINE-3-CARBOXYLIC ACID, A CONFORMATIONALLY CONSTRAINED TYROSINE ANALOG

VERSCHUEREN, K; TOTH, G; TOURWE, D; LEBL, M; VANBINST, G; HRUBY, V

A FACILE SYNTHESIS OF 1,2,3,4-TETRAHYDRO-7-HYDROXYISOQUINOLINE-3-CARBOXYLIC ACID, A CONFORMATIONALLY CONSTRAINED TYROSINE ANALOG

Author:

VERSCHUEREN, K

TOTH, G ; TOURWE, D ; LEBL, M ; VANBINST, G ; HRUBY, V

Keywords:

Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, 0301 Analytical Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3405 Organic chemistry

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.