Debromodispacamides B and D: isolation from the marine sponge Agelas mauritiana and stereoselective synthesis using a biomimetic proline route

Carine Vergne; Jérôme Appenzeller; Céline Ratinaud; Marie-Thérèse Martin; Cécile Debitus; Anne Zaparucha; Ali Al-Mourabit

doi:10.1021/ol702866m

Debromodispacamides B and D: isolation from the marine sponge Agelas mauritiana and stereoselective synthesis using a biomimetic proline route

Org Lett. 2008 Feb 7;10(3):493-6. doi: 10.1021/ol702866m. Epub 2008 Jan 3.

Authors

Carine Vergne¹, Jérôme Appenzeller, Céline Ratinaud, Marie-Thérèse Martin, Cécile Debitus, Anne Zaparucha, Ali Al-Mourabit

Affiliation

¹ Institut de Chimie des Substances Naturelles du CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.

PMID: 18171071
DOI: 10.1021/ol702866m

Abstract

New debromopyrrole-2-aminoimidazolones, debromodispacamide B (1) and debromodispacamide D (2) were isolated from the sponge Agelas mauritiana, collected in the Solomon Islands. A biomimetic one-step reaction from pseudopeptides 5 and 13 in presence of air oxygen and guanidine gave the chiral form of the natural product stereoselectively.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Agelas / chemistry*
Animals
Imidazoles / chemical synthesis
Imidazoles / chemistry
Imidazoles / isolation & purification*
Marine Biology
Molecular Structure
Proline / chemistry
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Pyrroles / isolation & purification*
Stereoisomerism

Substances

Imidazoles
Pyrroles
debromodispacamide B
debromodispacamide D
imidazolone
Proline