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Synfacts 2015; 11(5): 0457
DOI: 10.1055/s-0034-1380622
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Aeruginosin Natural Products

Contributor(s):
Erick M. Carreira
,
Alberto G. Kravina
Dailler D, Danoun G, Baudoin O * Université Claude Bernard Lyon 1, France
A General and Scalable Synthesis of Aeruginosin Marine Natural Products Based on Two Strategic C(sp3)–H Activation Reactions.

Angew. Chem. Int. Ed. 2015;
54: 4919-4922
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Publication History

Publication Date:
17 April 2015 (online)

 
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Key words

aeruginosin 98B - aeruginosin 298A - marine natural products - serine protease inhibitor - C(sp3)–H bond activation

Significance

The marine natural products of the aeruginosin family have been shown to possess high in vitro inhibition of serine proteases. In this communication by Baudoin and co-workers, a novel approach for the synthesis of the core structure using an uncommon C(sp3)–H bond activation is presented, culminating in the efficient total synthesis of aeruginosins 98B and 298A.


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Comment

The synthesis of B, used for the pivotal C–H bond activation step, was accomplished from dibromocyclohexene A in two steps. Previously reported conditions (Angew. Chem. Int. Ed. 2012, 51, 10399) gave the cyclization product C in 68% yield. Its elaboration into key precursor D allowed for the installation of the peptide as well as the guanidine side chain of both natural products.


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