Journal article

Publication year: 2008

Pages: 3005-3016

Journal: Tetrahedron

Volume number: 64

Issue number: 13

Open access status: Green

DOI Link: https://doi.org/10.1016/j.tet.2008.01.061

Publisher: Elsevier

Abstract: 

We report a synthetic route to ansa pyrrole amino acids via olefin ring-closing metathesis of diene precursors in the presence of Grubbs I catalyst. The dienes were prepared by Grignard addition to pyrrole sulfinyl imines. The success of the macrocyclic ring closure depends on the dienes structure and only in the case of the 13-membered compound 28 sufficient material could be isolated by preparative HPLC separation to investigate its structure spectroscopically. As also rationalized by our computations at the B3LYP/6-311+G(d,p)//B3LYP/6-31G(d) level of theory, 28 is configurationally stable.

Harvard Citation style: Dirscherl, G., Rosshenas, P., Schreiner, P., Lamaty, F. and König, B. (2008) Synthesis and structure of a heterocyclic ansa pyrrole amino acid, Tetrahedron, 64(13), pp. 3005-3016. https://doi.org/10.1016/j.tet.2008.01.061

APA Citation style: Dirscherl, G., Rosshenas, P., Schreiner, P., Lamaty, F., & König, B. (2008). Synthesis and structure of a heterocyclic ansa pyrrole amino acid. Tetrahedron. 64(13), 3005-3016. https://doi.org/10.1016/j.tet.2008.01.061