143115-93-9Relevant academic research and scientific papers
Divergent Synthesis of Aeruginosins Based on a C(sp3)￡H Activation Strategy
Dailler, David,Danoun, Grégory,Ourri, Benjamin,Baudoin, Olivier
, p. 9370 - 9379 (2015/06/30)
A general and scalable access to the aeruginosin family of marine natural products, exhibiting potent inhibitory activity against serine proteases, is reported. This was enabled by the strategic use of two recently implemented Pd-catalyzed C(sp3)￡H activation reactions. The first method allowed us to obtain the common 2-carboxy-6-hydroxyoctahydroindole (Choi) core of the target molecules on a large scale, whereas the second method provided a rapid and divergent access to various hydroxyphenyllactic (Hpla) subunits, including halogenated ones. This unique strategy, together with an optimization of the fragment coupling sequence allowed the synthesis of four aeruginosins, that is, 98A-C and 298A from the chiral pool. Among them, aeruginosin 298A was synthesized on an unprecedentedly large scale. In addition, halogenated aeruginosins 98A and 98C were synthesized for the first time, thanks to a fine-tuning of the final hydrogenation step. Go natural! A general and scalable access to the aeruginosin family of marine natural products (see graphic), exhibiting potent inhibitory activity against serine proteases, is described. The strategic use of two different Pd-catalyzed C(sp3)￡H activation reactions led to the synthesis of aeruginosins98A-C and 298A.
A general and scalable synthesis of aeruginosin marine natural products based on two strategic C(sp3)-H activation reactions
Dailler, David,Danoun, Grégory,Baudoin, Olivier
, p. 4919 - 4922 (2015/04/14)
An efficient and scalable access to the aeruginosin family of marine natural products, which exhibit potent inhibitory activity against serine proteases, is reported. This synthesis was enabled by the strategic use of two different, recently implemented C(sp3)-H activation reactions. The first method led to the common 2-carboxy-6-hydroxyoctahydroindole (Choi) core of the target molecules on a large scale, whereas the second one provided rapid and divergent access to the various hydroxyphenyllactic (Hpla) subunits. This strategy allowed the synthesis of the aeruginosins 98B and 298A, with the latter being obtained in unprecedentedly large quantities.
RTD-1 mimic containing γPNA scaffold exhibits broad-spectrum antibacterial activities
Rapireddy, Srinivas,Nhon, Linda,Meehan, Robert E.,Franks, Jonathan,Stolz, Donna Beer,Tran, Dat,Selsted, Michael E.,Ly, Danith H.
, p. 4041 - 4044 (2012/04/10)
Macrocyclic peptides with multiple disulfide cross-linkages, such as those produced by plants and those found in nonhuman primates, as components of the innate immunity, hold great promise for molecular therapy because of their broad biological activities
