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Total Synthesis of (−)-Cylindricine H
[Image: see text] Starting from (R)-phenylglycinol-derived tricyclic lactam 1, the enantioselective synthesis of (−)-cylindricine H is reported. From the stereochemical standpoint, the key steps are the stereoselective generation of the quaternary C(10) stereocenter, the stereoselective introduction...
| Autores principales: | , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2022
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9881165/ https://www.ncbi.nlm.nih.gov/pubmed/35849750 http://dx.doi.org/10.1021/acs.orglett.2c02004 |
| _version_ | 1784879055837855744 |
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| author | Piccichè, Miriam Pinto, Alexandre Griera, Rosa Bosch, Joan Amat, Mercedes |
| author_facet | Piccichè, Miriam Pinto, Alexandre Griera, Rosa Bosch, Joan Amat, Mercedes |
| author_sort | Piccichè, Miriam |
| collection | PubMed |
| description | [Image: see text] Starting from (R)-phenylglycinol-derived tricyclic lactam 1, the enantioselective synthesis of (−)-cylindricine H is reported. From the stereochemical standpoint, the key steps are the stereoselective generation of the quaternary C(10) stereocenter, the stereoselective introduction of the C(4) acetoxy and C(2) butyl substituents taking advantage of the lactam carbonyl functionality, and the assembly of the pyrrolidine ring with the required functionalized one-carbon chain at C(13) by intramolecular opening of an epoxide. |
| format | Online Article Text |
| id | pubmed-9881165 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2022 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-98811652023-01-28 Total Synthesis of (−)-Cylindricine H Piccichè, Miriam Pinto, Alexandre Griera, Rosa Bosch, Joan Amat, Mercedes Org Lett [Image: see text] Starting from (R)-phenylglycinol-derived tricyclic lactam 1, the enantioselective synthesis of (−)-cylindricine H is reported. From the stereochemical standpoint, the key steps are the stereoselective generation of the quaternary C(10) stereocenter, the stereoselective introduction of the C(4) acetoxy and C(2) butyl substituents taking advantage of the lactam carbonyl functionality, and the assembly of the pyrrolidine ring with the required functionalized one-carbon chain at C(13) by intramolecular opening of an epoxide. American Chemical Society 2022-07-18 /pmc/articles/PMC9881165/ /pubmed/35849750 http://dx.doi.org/10.1021/acs.orglett.2c02004 Text en © 2022 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Piccichè, Miriam Pinto, Alexandre Griera, Rosa Bosch, Joan Amat, Mercedes Total Synthesis of (−)-Cylindricine H |
| title | Total Synthesis
of (−)-Cylindricine H |
| title_full | Total Synthesis
of (−)-Cylindricine H |
| title_fullStr | Total Synthesis
of (−)-Cylindricine H |
| title_full_unstemmed | Total Synthesis
of (−)-Cylindricine H |
| title_short | Total Synthesis
of (−)-Cylindricine H |
| title_sort | total synthesis
of (−)-cylindricine h |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9881165/ https://www.ncbi.nlm.nih.gov/pubmed/35849750 http://dx.doi.org/10.1021/acs.orglett.2c02004 |
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