Bicyclo[3.3.1]nonanes as synthetic intermediates XIII. : Novel transannular hydride shifts enforced by relief of the steric constraint in the bicyclo[3.3.1]nonane system bearing endo-substituents at position 7 |
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| Institution: | 1. Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000 Novi Sad, Serbia;2. Oncology Institute of Vojvodina, Faculty of Medicine, University of Novi Sad, Put Dr Goldmana 4, 21204 Sremska Kamenica, Serbia;3. Department of Pharmacy, Faculty of Medicine, University of Novi Sad, Hajduk Veljka 3, 21000 Novi Sad, Serbia;4. Department of Physics, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 4, 21000 Novi Sad, Serbia |
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| Abstract: | The Huang-Minlon reduction of 7α-hydroxymethylbicycl4o3.3.1]- nonan-3-one (1) gave 7β-methylbicyclo3.3.1]nonan-3 β-ol (2), a product formed as a result of the transannular 1,6-hydride shift enforced by relief of the stenc constraint in the system. Another example of the intramolecular hydride transfer on the same basis was observed in the deketalization of 9,9-disubstituted 7,7-ethylenedioxybicyclo3.3.1 ]- nonan-3 β-ol (13 and 18) resulting in the formation of 7 β-(2-hydroxyethoxy) bicyclo3.3.1]nonan-3-one (15 and 20). |
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