Total synthesis of ageliferin via acyl N-amidinyliminium ion rearrangement

Autor:	Patrick G. Harran, Hui Ding, Andrew G. Roberts
Rok vydání:	2013
Předmět:	chemistry.chemical_compound Natural product Molecular level chemistry Axinellamine Imidazole Total synthesis General Chemistry Combinatorial chemistry Article Ageliferin Ion Pyrrole
Zdroj:	Chem. Sci.. 4:303-306
ISSN:	2041-6539 2041-6520
DOI:	10.1039/c2sc21651e
Popis:	Ageliferin is a marine natural product having antiviral and antimicrobial activities. These functions remain to be characterized at a molecular level. Ageliferin is also thought a biosynthetic intermediary linking oroidin type alkaloids to more complex polycyclic derivatives. This scenario has the amino tetrahydrobenzimidazole motif in ageliferin serving as a reduced progenitor of oxidized, ring-contracted spirocycles. Here we describe the reverse. Namely, a concise synthesis of ageliferin which features ring expansion of a spirocyclic precursor - itself derived from reduction. The pathway also provides access to unique isosteres of the axinellamine ring system, allowing new synthetic additions to the growing family of pyrrole / imidazole alkaloids.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4a2ab7a8f8eab44082fb2bc5b7b6009c https://doi.org/10.1039/c2sc21651e Zobrazit plný text záznamu