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Synfacts 2015; 11(1): 0005
DOI: 10.1055/s-0034-1379679
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Biology of Axinellamines A and B

Contributor(s):
Erick M. Carreira
,
Matthias Westphal
Rodriguez RA, Steed DB, Kawamata Y, Su S, Smith PA, Steed TC, Romesberg FE, * Baran PS. * The Scripps Research Institute, La Jolla, RQx Pharmaceuticals, La Jolla, and University of California, San Diego, USA
Axinellamines as Broad-Spectrum Antibacterial Agents: Scalable Synthesis and Biology.

J. Am. Chem. Soc. 2014;
136: 15403-15413
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

axinellamines - antibiotics - Pauson–Khand reaction - chlorospirocyclization

Significance

Pyrrole–imidazole alkaloids are a class of complex natural products with intriguing biological activities, isolated from marine sponges. The authors present a full account of their synthetic efforts to derive substantial quantities of racemic axinellamines A and B. In addition, valuable follow-up biological studies showing antibiotic activity against Gram-positive and -negative bacteria are presented.


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Comment

The authors disclose details of recent work directed towards the efficient synthesis of axinellamines A and B (J. Am. Chem. Soc. 2011, 133, 13922). A ­Pauson–Khand reaction afforded cyclopentene C, which could be efficiently converted into diazide G. Oxidative cyclization, deprotection, and imidazole formation followed by a dihydroxylation–dehydration sequence led to J. Silver(II)-mediated oxidation, azide reduction, and amidation afforded the two targets.


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