6-Substituted 2-azabicyclo[2.2.1]hept-5-enes by nitrogen-directed radical rearrangement: Synthesis of an epibatidine analogue with high binding affinity at the nicotinic acetylcholine receptor
Base-induced isomerisation of epoxide 13 gives an azanortricyclanol 17 which is a precursor for a novel free-radical induced rearrangement to 6-substituted 2-azabicyclo[2.2.1]hept-5-enes 28-31. Compound 31 undergoes selective exo-face hydrogenation to give the 6-substituted 2-azabicyclo[2.2.1]heptan...
| Автори: | , , , , , , |
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| Формат: | Journal article |
| Мова: | English |
| Опубліковано: |
2001
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| _version_ | 1826297420936380416 |
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| author | Hodgson, D Maxwell, C Wisedale, R Matthews, I Carpenter, K Dickenson, A Wonnacott, S |
| author_facet | Hodgson, D Maxwell, C Wisedale, R Matthews, I Carpenter, K Dickenson, A Wonnacott, S |
| author_sort | Hodgson, D |
| collection | OXFORD |
| description | Base-induced isomerisation of epoxide 13 gives an azanortricyclanol 17 which is a precursor for a novel free-radical induced rearrangement to 6-substituted 2-azabicyclo[2.2.1]hept-5-enes 28-31. Compound 31 undergoes selective exo-face hydrogenation to give the 6-substituted 2-azabicyclo[2.2.1]heptane 33 (structure confirmed by X-ray crystallographic analysis). Deprotection of 33 gives epibatidine analogue 2 which has been shown to bind with high affinity at rat brain nicotinic acetylcholine receptors. |
| first_indexed | 2024-03-07T04:31:21Z |
| format | Journal article |
| id | oxford-uuid:ce6e5f1d-2092-446c-a407-e43ac4dfb41d |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:31:21Z |
| publishDate | 2001 |
| record_format | dspace |
| spelling | oxford-uuid:ce6e5f1d-2092-446c-a407-e43ac4dfb41d2022-03-27T07:35:32Z6-Substituted 2-azabicyclo[2.2.1]hept-5-enes by nitrogen-directed radical rearrangement: Synthesis of an epibatidine analogue with high binding affinity at the nicotinic acetylcholine receptorJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:ce6e5f1d-2092-446c-a407-e43ac4dfb41dEnglishSymplectic Elements at Oxford2001Hodgson, DMaxwell, CWisedale, RMatthews, ICarpenter, KDickenson, AWonnacott, SBase-induced isomerisation of epoxide 13 gives an azanortricyclanol 17 which is a precursor for a novel free-radical induced rearrangement to 6-substituted 2-azabicyclo[2.2.1]hept-5-enes 28-31. Compound 31 undergoes selective exo-face hydrogenation to give the 6-substituted 2-azabicyclo[2.2.1]heptane 33 (structure confirmed by X-ray crystallographic analysis). Deprotection of 33 gives epibatidine analogue 2 which has been shown to bind with high affinity at rat brain nicotinic acetylcholine receptors. |
| spellingShingle | Hodgson, D Maxwell, C Wisedale, R Matthews, I Carpenter, K Dickenson, A Wonnacott, S 6-Substituted 2-azabicyclo[2.2.1]hept-5-enes by nitrogen-directed radical rearrangement: Synthesis of an epibatidine analogue with high binding affinity at the nicotinic acetylcholine receptor |
| title | 6-Substituted 2-azabicyclo[2.2.1]hept-5-enes by nitrogen-directed radical rearrangement: Synthesis of an epibatidine analogue with high binding affinity at the nicotinic acetylcholine receptor |
| title_full | 6-Substituted 2-azabicyclo[2.2.1]hept-5-enes by nitrogen-directed radical rearrangement: Synthesis of an epibatidine analogue with high binding affinity at the nicotinic acetylcholine receptor |
| title_fullStr | 6-Substituted 2-azabicyclo[2.2.1]hept-5-enes by nitrogen-directed radical rearrangement: Synthesis of an epibatidine analogue with high binding affinity at the nicotinic acetylcholine receptor |
| title_full_unstemmed | 6-Substituted 2-azabicyclo[2.2.1]hept-5-enes by nitrogen-directed radical rearrangement: Synthesis of an epibatidine analogue with high binding affinity at the nicotinic acetylcholine receptor |
| title_short | 6-Substituted 2-azabicyclo[2.2.1]hept-5-enes by nitrogen-directed radical rearrangement: Synthesis of an epibatidine analogue with high binding affinity at the nicotinic acetylcholine receptor |
| title_sort | 6 substituted 2 azabicyclo 2 2 1 hept 5 enes by nitrogen directed radical rearrangement synthesis of an epibatidine analogue with high binding affinity at the nicotinic acetylcholine receptor |
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