Stereoselective synthesis of 2,4-methanoproline homologues |
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| Institution: | 1. Department of Chemistry, Kyiv Taras Shevchenko University, Volodymyrska Street, 64, Kyiv 01033, Ukraine;2. STC ‘Institute for Single Crystals’ National Academy of Science of Ukraine, 60 Lenina ave., Kharkiv 61001, Ukraine;3. Enamine Ltd, Alexandra Matrosova Street, 23, Kyiv 01103, Ukraine;1. Medicinal and Chemical Institute, China Pharmaceutical University, Nanjing 210009, PR China;2. Department of Medicinal Chemistry, University of Florida, Gainesville, FL 32610, United States;3. State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Carcinogenesis and Intervention, China Pharmaceutical University, Nanjing 210009, PR China;1. National Taras Shevchenko University of Kyiv, Volodymyrska Street, 64, Kyiv 01601, Ukraine;2. Enamine Ltd, Alexandra Matrosova Street, 23, Kyiv 01103, Ukraine;1. Unité de Catalyse et de Chimie du Solide (UCCS), CNRS, UMR 8181, Université d’Artois, Rue Jean Souvraz, SP 18, F-62307 Lens, France;2. Unité de Chimie Environnementale et Interactions sur le Vivant (UCEIV)—EA 4492, Université du Littoral Côte d’Opâle 145, Avenue Maurice Schumann, MREI 1, F-59140 Dunkerque, France |
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| Abstract: | The stereoselective synthesis of 2-azabicyclo2.2.1]heptane-1-carboxylic acid and 6-azabicyclo3.2.1]octane-5-carboxylic acid, novel rigid bicyclic proline analogues, is reported. The synthesis was performed in five steps from the corresponding 2-cycloalken-1-ones. A known approach to 2,4-methanoproline is improved. The three amino acids constitute a library of conformationally constrained proline analogues, which can be used for the design of peptidomimetics and peptide models. |
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