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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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Further Information

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.


 

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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