Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds
ABSTRACT: The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C–3, C–8 and C–9, and a 1,6-double bond has been accomplished in 10 steps with an overall 17% yield. This compound is a key intermediate for access to a wide range of compounds of the bioactive tr...
- Autores:
-
González Delgado, José Antonio
Escobar Peláez, Gustavo
Fernández Arteaga, Jesús
Fernández Barrero, Alejandro
- Tipo de recurso:
- Article of investigation
- Fecha de publicación:
- 2014
- Institución:
- Universidad de Antioquia
- Repositorio:
- Repositorio UdeA
- Idioma:
- eng
- OAI Identifier:
- oai:bibliotecadigital.udea.edu.co:10495/23689
- Acceso en línea:
- http://hdl.handle.net/10495/23689
- Palabra clave:
- Trisporoides
Apocarotenoid
Stereoselective synthesis
Reacción dominó
- Rights
- openAccess
- License
- http://creativecommons.org/licenses/by/2.5/co/
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Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds |
| title |
Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds |
| spellingShingle |
Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds Trisporoides Apocarotenoid Stereoselective synthesis Reacción dominó |
| title_short |
Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds |
| title_full |
Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds |
| title_fullStr |
Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds |
| title_full_unstemmed |
Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds |
| title_sort |
Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds |
| dc.creator.fl_str_mv |
González Delgado, José Antonio Escobar Peláez, Gustavo Fernández Arteaga, Jesús Fernández Barrero, Alejandro |
| dc.contributor.author.none.fl_str_mv |
González Delgado, José Antonio Escobar Peláez, Gustavo Fernández Arteaga, Jesús Fernández Barrero, Alejandro |
| dc.contributor.researchgroup.spa.fl_str_mv |
Química Orgánica de Productos Naturales |
| dc.subject.proposal.spa.fl_str_mv |
Trisporoides Apocarotenoid Stereoselective synthesis Reacción dominó |
| topic |
Trisporoides Apocarotenoid Stereoselective synthesis Reacción dominó |
| description |
ABSTRACT: The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C–3, C–8 and C–9, and a 1,6-double bond has been accomplished in 10 steps with an overall 17% yield. This compound is a key intermediate for access to a wide range of compounds of the bioactive trisporoid family. The synthetic sequence consists of the preparation of a properly functionalized epoxygeraniol derivative, and its subsequent stereoselective cyclization mediated by Ti(III). This last step implies a domino process that starts with a homolytic epoxide opening followed by a radical cyclization and regioselective elimination. This concerted process gives access to the cyclohexane moiety with stereochemical control of five of its six carbon atoms. |
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2014 |
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2014 |
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2021-11-02T14:57:58Z |
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2021-11-02T14:57:58Z |
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Artículo de investigación |
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González, J., Escobar, G., Arteaga, J., & Barrero, A. (2014). Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds. Molecules, 19(2), 1748–1762. Retrieved from http://dx.doi.org/10.3390/molecules19021748 |
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http://hdl.handle.net/10495/23689 |
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10.3390/molecules19021748 |
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1420-3049 |
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González, J., Escobar, G., Arteaga, J., & Barrero, A. (2014). Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds. Molecules, 19(2), 1748–1762. Retrieved from http://dx.doi.org/10.3390/molecules19021748 10.3390/molecules19021748 1420-3049 |
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http://hdl.handle.net/10495/23689 |
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eng |
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eng |
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Molecules |
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1762 |
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2 |
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1748 |
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19 |
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Molecules |
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http://creativecommons.org/licenses/by/2.5/co/ |
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Basilea, Suiza |
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González Delgado, José AntonioEscobar Peláez, GustavoFernández Arteaga, JesúsFernández Barrero, AlejandroQuímica Orgánica de Productos Naturales2021-11-02T14:57:58Z2021-11-02T14:57:58Z2014González, J., Escobar, G., Arteaga, J., & Barrero, A. (2014). Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds. Molecules, 19(2), 1748–1762. Retrieved from http://dx.doi.org/10.3390/molecules19021748http://hdl.handle.net/10495/2368910.3390/molecules190217481420-3049ABSTRACT: The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C–3, C–8 and C–9, and a 1,6-double bond has been accomplished in 10 steps with an overall 17% yield. This compound is a key intermediate for access to a wide range of compounds of the bioactive trisporoid family. The synthetic sequence consists of the preparation of a properly functionalized epoxygeraniol derivative, and its subsequent stereoselective cyclization mediated by Ti(III). This last step implies a domino process that starts with a homolytic epoxide opening followed by a radical cyclization and regioselective elimination. This concerted process gives access to the cyclohexane moiety with stereochemical control of five of its six carbon atoms.COL001533915application/pdfengMDPIBasilea, Suizahttp://creativecommons.org/licenses/by/2.5/co/https://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related CompoundsArtículo de investigaciónhttp://purl.org/coar/resource_type/c_2df8fbb1https://purl.org/redcol/resource_type/ARThttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionTrisporoidesApocarotenoidStereoselective synthesisReacción dominóMolecules17622174819MoleculesPublicationORIGINALEscobarGustavo_2014_SynthesisTrisporicAcids.pdfEscobarGustavo_2014_SynthesisTrisporicAcids.pdfArtículo de investigaciónapplication/pdf430560https://bibliotecadigital.udea.edu.co/bitstreams/74df896e-a315-4adb-8636-14e3d6a2891d/download9a764ef44f5791d84b4c672cfedb5334MD51trueAnonymousREADCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8927https://bibliotecadigital.udea.edu.co/bitstreams/4f67bea1-f4d1-4e78-b73e-2e59e0ac06d8/download1646d1f6b96dbbbc38035efc9239ac9cMD52falseAnonymousREADLICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://bibliotecadigital.udea.edu.co/bitstreams/f73ac35e-00eb-48cd-b68f-6cc9b6090df7/download8a4605be74aa9ea9d79846c1fba20a33MD53falseAnonymousREADTEXTEscobarGustavo_2014_SynthesisTrisporicAcids.pdf.txtEscobarGustavo_2014_SynthesisTrisporicAcids.pdf.txtExtracted texttext/plain41100https://bibliotecadigital.udea.edu.co/bitstreams/5d1834ae-3312-43c4-ac3a-61191e121437/download44477141ca2f8770710537cb35ba0a1eMD54falseAnonymousREADTHUMBNAILEscobarGustavo_2014_SynthesisTrisporicAcids.pdf.jpgEscobarGustavo_2014_SynthesisTrisporicAcids.pdf.jpgGenerated Thumbnailimage/jpeg13707https://bibliotecadigital.udea.edu.co/bitstreams/48c219df-bc60-4f94-bdff-b37cda564344/download1d52dee709415b790c875a4d2df2428bMD55falseAnonymousREAD10495/23689oai:bibliotecadigital.udea.edu.co:10495/236892025-03-27 00:05:38.332http://creativecommons.org/licenses/by/2.5/co/open.accesshttps://bibliotecadigital.udea.edu.coRepositorio Institucional de la Universidad de Antioquiaaplicacionbibliotecadigitalbiblioteca@udea.edu.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 |