Abstract
Pd-catalyzed allylations of cyclic bis-allylic substrates, carried out either as two separate steps or in a pseudo-domino fashion, can generate 2-carboxyl-hexahydroindoles bearing an unsaturation in different positions. Sequential homologation, and epoxidation or syn-dihydroxylation steps were investigated to access analogues of the bicyclic 2-carboxyl-6-hydroxyoctahydroindole motif of aeruginosins, a family of peptides displaying serine protease inhibitor activity.
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