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Issue 1, 2013

Total synthesis of ageliferin via acyl N-amidinyliminium ion rearrangement

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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.

Graphical abstract: Total synthesis of ageliferin via acyl N-amidinyliminium ion rearrangement

Supplementary files

Article information


Submitted
03 Oct 2012
Accepted
24 Oct 2012
First published
24 Oct 2012

Chem. Sci., 2013,4, 303-306
Article type
Edge Article

Total synthesis of ageliferin via acyl N-amidinyliminium ion rearrangement

H. Ding<small xmlns="http://www.rsc.org/schema/rscart38"> <sup /> </small>, A. G. Roberts<small xmlns="http://www.rsc.org/schema/rscart38"> <sup /> </small> and P. G. Harran, Chem. Sci., 2013, 4, 303 DOI: 10.1039/C2SC21651E

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