Convenient synthesis of 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and its derivatives as doubly constrained nonproteinogenic amino acid derivatives

Convenient synthesis of 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and its derivatives as doubly constrained nonproteinogenic amino acid derivatives Full article

Journal

Journal of Organic Chemistry
ISSN: 0022-3263

Output data

Year: 2000, Volume: 65, Number: 18, Pages: 5469-5475 Pages count : DOI: 10.1021/jo9917994

Authors

Czombos J , Aelterman W , Tkachev A , Martins JC , Tourwe D , Peter A , Toth G , Fulop F , De Kimpe N

Affiliations

1	(Данные Web of science) State Univ Ghent, Fac Agr & Appl Biol Sci, Dept Organ Chem, B-9000 Ghent, Belgium
2	(Данные Web of science) Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
3	(Данные Web of science) Free Univ Brussels, HNMR Ctr, B-1050 Brussels, Belgium
4	(Данные Web of science) Free Univ Brussels, Organ Chem Lab, B-1050 Brussels, Belgium
5	(Данные Web of science) Univ Szeged, Dept Inorgan & Analyt Chem, H-6701 Szeged, Hungary
6	(Данные Web of science) Hungarian Acad Sci, Isotope Lab, Biol Res Ctr, H-6701 Szeged, Hungary
7	(Данные Web of science) Univ Szeged, Inst Pharmaceut Chem, H-6701 Szeged, Hungary

Three strategies for the synthesis of the novel, doubly constrained, 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and its derivatives were evaluated. Only cyclocondensation of the mono(triphenyl)phosphonium salt derived from 1,2-bis(bromomethyl)benzene with N-alkoxycarbonyloxamates in 1,2-dimethoxyethane in the presence of potassium carbonate and subsequent cyclopropanation with dimethylsulfoxonium methylide in dimethyl sulfoxide furnished suitable O-and N-protected derivatives of 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in a convenient way. A detailed 2D DQF-COSY and 2D NOESY NMR analysis of the rotational. isomerism of the latter bicyclic amino acid derivatives was performed. Various O- and N-protection protocols were worked out to afford access to a whole range of new derivatives of the title amino acid, suitable for peptide synthesis.

Czombos J. , Aelterman W. , Tkachev A. , Martins J. , Tourwe D. , Peter A. , Toth G. , Fulop F. , De Kimpe N.
Convenient synthesis of 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and its derivatives as doubly constrained nonproteinogenic amino acid derivatives
Journal of Organic Chemistry. 2000. V.65. N18. P.5469-5475. DOI: 10.1021/jo9917994 WOS Scopus РИНЦ OpenAlex

Published print:

Sep 1, 2000

Web of science:	WOS:000089310200003
Scopus:	2-s2.0-0033824636
Elibrary:	13334810
OpenAlex:	W2084817145

DB	Citing
Web of science	26
Scopus	28
Elibrary	28
OpenAlex	27