A NEW SYNTHESIS OF CYCLOTHEONAMIDE-B VIA GUANIDINATION OF ORNITHINE

Authors
DENG JG HAMADA Y SHIOIRI T
Citation
Jg. Deng et al., A NEW SYNTHESIS OF CYCLOTHEONAMIDE-B VIA GUANIDINATION OF ORNITHINE, Tetrahedron letters, 37(13), 1996, pp. 2261-2264
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
13
Year of publication
1996
Pages
2261 - 2264
Database
ISI
SICI code
0040-4039(1996)37:13<2261:ANSOCV>2.0.ZU;2-7
Abstract
A macrocyclic thrombin inhibitor, cyclotheonamide B (1, R=Ac) was synt hesized via a new approach: guanidination of the ornithine-containing macrocyclic peptide (2). In comparison of various coupling reagents, p entafluorophenyl diphenylphosphinate (FDPP) gave the macrocyclic pepti de (2) in good yield, and the configuration of the amino acid residue has been revealed to be important for the macrolactamization.