167228-01-5Relevant academic research and scientific papers
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.
Total synthesis of aeruginosin 98B
Trost, Barry M.,Kaneko, Toshiyuki,Andersen, Neil G.,Tappertzhofen, Christoph,Fahr, Bruce
, p. 18944 - 18947 (2013/01/15)
The first total synthesis of aeruginosin 98B was accomplished. The key step is a highly diastereoselective Pd-catalyzed intramolecular asymmetric allylic alkylation reaction of a diastereomeric mixture of allylic carbonates that is enabled by the use of racemic phosphine ligand L1.
