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Total Synthesis of Ageliferin via Acyl N-amidinyliminium Ion Rearrangement.

ABSTRACT: 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.

SUBMITTER: Ding H

PROVIDER: S-EPMC3653441 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Total Synthesis of Ageliferin via Acyl N-amidinyliminium Ion Rearrangement.

Ding Hui H Roberts Andrew G AG Harran Patrick G PG

Chemical science 20130101 1

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 ...[more]

PMID: 23687567

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