Journal
TETRAHEDRON LETTERS
Volume 58, Issue 44, Pages 4174-4178Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.09.046
Keywords
Palladium catalysis; CHOI core; Allylic substitution; Domino reaction; Stereoselective synthesis
Categories
Funding
- CNRS
- UPMC
- Labex Michem
- CMST COST Action [CA15106]
- Erasmus Mundus Europe Asia (EMEA)
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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. (C) 2017 Elsevier Ltd. All rights reserved.
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