Analogues of the 2-carboxyl-6-hydroxyoctahydroindole (CHOI) unit from diverging Pd-catalyzed allylations: Selectivity as a function of the double bond position
| Autor: | Elisabetta Martini, Zhong-Yi Mao, Pei-Qiang Huang, Giovanni Poli, Julie Oble, Guillaume Prestat |
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| Přispěvatelé: | Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Xiamen University, Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2017 |
| Předmět: |
Double bond
Stereochemistry Serine protease inhibitor activity 010402 general chemistry 01 natural sciences Biochemistry Catalysis Drug Discovery chemistry.chemical_classification Degree of unsaturation Bicyclic molecule [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry organic chemicals Organic Chemistry Stereoselective synthesis Domino reaction food and beverages [CHIM.CATA]Chemical Sciences/Catalysis Allylic substitution Palladium catalysis 0104 chemical sciences chemistry CHOI core Selectivity Function (biology) |
| Zdroj: | Tetrahedron Letters Tetrahedron Letters, Elsevier, 2017, 58 (44), pp.4174-4178. ⟨10.1016/j.tetlet.2017.09.046⟩ Tetrahedron Letters, 2017, 58 (44), pp.4174-4178. ⟨10.1016/j.tetlet.2017.09.046⟩ |
| ISSN: | 0040-4039 1873-3581 |
| DOI: | 10.1016/j.tetlet.2017.09.046 |
| Popis: | International audience; 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. |
| Databáze: | OpenAIRE |
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