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(sp
3)–H Activation Reactions.
Angew. Chem. Int. Ed. 2015;
54: 4919-4922
Key words
aeruginosin 98B - aeruginosin 298A - marine natural products - serine protease inhibitor - C(sp
3)–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.
