Total Synthesis of Ageliferin Via Acyl N-amidinyliminium Ion Rearrangement

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2013 May 21

PMID 23687567

Citations 7

Authors

Hui Ding

Andrew G Roberts

Patrick G Harran

Affiliations

Soon will be listed here.

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.

Citing Articles

Stereocontrolled Formation of a [4.4]Heterospiro Ring System with Unexpected Inversion of Configuration at the Spirocenter.

Ma Z, You L, Chen C J Org Chem. 2016; 82(1):731-736.

PMID: 27933858 PMC: 5527678. DOI: 10.1021/acs.joc.6b02266.

Asymmetric Synthesis of Axinellamines A and B.

Ma Z, Wang X, Ma Y, Chen C Angew Chem Int Ed Engl. 2016; 55(15):4763-6.

PMID: 27037993 PMC: 4836294. DOI: 10.1002/anie.201600007.

Syntheses of Sceptrins and Nakamuric Acid and Insights into the Biosyntheses of Pyrrole-Imidazole Dimers.

Wang X, Gao Y, Ma Z, Rodriguez R, Yu Z, Chen C Org Chem Front. 2015; 2(8):978-984.

PMID: 26328059 PMC: 4551504. DOI: 10.1039/C5QO00165J.

Syntheses of Cyclic Guanidine-Containing Natural Products.

Ma Y, De S, Chen C Tetrahedron. 2015; 71(8):1145-1173.

PMID: 25684829 PMC: 4325426. DOI: 10.1016/j.tet.2014.11.056.

Axinellamines as broad-spectrum antibacterial agents: scalable synthesis and biology.

Rodriguez R, Steed D, Kawamata Y, Su S, Smith P, Steed T J Am Chem Soc. 2014; 136(43):15403-13.

PMID: 25328977 PMC: 4227811. DOI: 10.1021/ja508632y.

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