title: A general and scalable synthesis of aeruginosin marine natural products based on two strategic C(sp³)-H activation reactions.
abstract: 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.
authors.affiliation: Université Claude Bernard Lyon 1, CNRS UMR 5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CPE Lyon, 43 Boulevard du 11 Novembre 1918 (France) http://cosmo.univ-lyon1.fr/Index.html.
authors.forename: David
authors.initials: D
authors.lastname: Dailler
authors.forename: Grégory
authors.initials: G
authors.lastname: Danoun
authors.forename: Olivier
authors.initials: O
authors.lastname: Baudoin
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D006859:Hydrogen / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D007930:Leucine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D007211:Indoles; D009842:Oligopeptides; C419325:aeruginosin 298-A; C472547:aeruginosin 98-B; D010165:Palladium; D002244:Carbon; D006859:Hydrogen; D007930:Leucine
keywords: CH activation; natural products; palladium; synthetic methods; total synthesis