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A General and Scalable Synthesis of Aeruginosin Marine Natural Products Based on Two Strategic C(sp 3 )H Activation Reactions
Author(s) -
Dailler David,
Danoun Grégory,
Baudoin Olivier
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500066
Subject(s) - chemistry , proteases , serine , catalysis , combinatorial chemistry , molecule , stereochemistry , enzyme , biochemistry , organic chemistry
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(sp 3 )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.