Novel heterocyclic Tröger's base derivatives containing N-methylpyrrole units

• Published in: Tetrahedron letters 2003-03, Vol.44 (10), p.2083-2086
• Main Authors: Valı&#x0301, k, Martin, Dolensky, Bohumil, Petřı&#x0301, čková, Hana, Vašek, Petr, Král, Vladimı&#x0301, r
• Format: Article
• Language: English
• Subjects: guanidine; N-methylpyrrole; regioselectivity; Tröger's base
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(03)00177-1

Novel analogues of Tröger's base were prepared regioselectively from 4-amino- N-methylpyrrole carboxylates in good yield. Catalytic hydrogenation of dibenzyl-4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1 H,6 H-dipyrrolo-[3,2- b:3′,2′- f][1,5]diazocin-2,7-dicarboxylate 2b led to 4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1 H,6 H-dipyrrolo-[3,2- b:3′,2′- f][1,5]diazocin-2,7-dicarboxylic acid 3 which was used for the preparation of Tröger's base derivatives of natural antibiotics via an amide protocol. The novel heterocyclic Tröger's bases were characterized by a variety of spectroscopic techniques and compound 2b by X-ray crystallography. Incorporation of guanidine as the terminal group in the N-methylpyrrole Tröger's base skeleton opens the possibility for preparation of water soluble derivatives. Novel analogues of Tröger's base were prepared regioselectively from 4-amino- N-methylpyrrole carboxylates in good yield. The dicarboxylic acid derivative (R=H) was used for the preparation of Tröger's base derivatives of natural antibiotics via an amide protocol. Incorporation of guanidine as the terminal group in the N-methylpyrrole Tröger's base skeleton opens the possibility of the preparation of water soluble derivatives.