Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions
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Abstract
- The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η4-diene complex with Fe(CO)3) in a short sequence of steps: 1) nucleophilic amine addition and subsequent Boc-protection, 2) photochemical demetallation of the iron complex, and 3) an intramolecular Heck reaction. Minor modifications to the protocol enabled access to the related 2-azabicyclo[4.4.1]undecane system, albeit in lower yield.
| Title | Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions |
|---|---|
| Creator | Beitel, S. K. |
| Uttaro, E. P. | |
| Griffith, Daniel R. | |
| Shoemaker, A. H. | |
| Foker, E. A. | |
| Publisher | Beilstein Journal of Organic Chemistry |
| Academic Department | Chemistry |
| Division | Natural Sciences |
| Organization | Lafayette College |
| Date Issued | 2023 |
| Date Available | 2023-12-19 |
| Type | Article |
| Language | English |
| Keyword | alkaloids |
| azabicycles | |
| Heck reaction | |
| tropone | |
| iron complex | |
| Bibliographic Citation | Shoemaker, A. H., et al. (2023) "Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions." Beilstein Journal of Organic Chemistry 19: 1615–1619. |
| Standard Identifier | DOI 10.3762/bjoc.19.118 |
| Handle 10385/kk91fm99f | |
| Permalink | http://hdl.handle.net/10385/kk91fm99f |
| Rights Statement |
Creative Commons - Attribution
|
| Rights Holders | Shoemaker, A. H. |
| Foker, E. A. | |
| Beitel, S. K. | |
| Griffith, Daniel R. | |
| Uttaro, E. P. |
Contains
| File | Griffith-BeilsteinJournalofOrganicChemistry-vol19-2023.pdf | Uploaded 2023-12-19 | Public | Download |
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