Cargando…
Synthesis and Stereochemical Assignment of (+)-Chamuvarinin
[Image: see text] A stereocontrolled total synthesis of (+)-chamuvarinin, isolated from the root extract of Uvaria Chamae, utilizes a convergent modular strategy to construct the adjacently linked C15−C28 ether array, followed by a late-stage Julia−Kocienski olefination to append the butenolide moti...
| Autores principales: | , , , , , |
|---|---|
| Formato: | Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2010
|
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3031177/ https://www.ncbi.nlm.nih.gov/pubmed/21174397 http://dx.doi.org/10.1021/ol1028699 |
| _version_ | 1782197319843708928 |
|---|---|
| author | Florence, Gordon J. Morris, Joanne C. Murray, Ross G. Osler, Jonathan D. Reddy, Vanga R. Smith, Terry K. |
| author_facet | Florence, Gordon J. Morris, Joanne C. Murray, Ross G. Osler, Jonathan D. Reddy, Vanga R. Smith, Terry K. |
| author_sort | Florence, Gordon J. |
| collection | PubMed |
| description | [Image: see text] A stereocontrolled total synthesis of (+)-chamuvarinin, isolated from the root extract of Uvaria Chamae, utilizes a convergent modular strategy to construct the adjacently linked C15−C28 ether array, followed by a late-stage Julia−Kocienski olefination to append the butenolide motif. This constitutes the first total synthesis of (+)-chamuvarinin, defining the relative and absolute configuration of this unique annonaceous acetogenin. |
| format | Text |
| id | pubmed-3031177 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2010 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-30311772011-01-31 Synthesis and Stereochemical Assignment of (+)-Chamuvarinin Florence, Gordon J. Morris, Joanne C. Murray, Ross G. Osler, Jonathan D. Reddy, Vanga R. Smith, Terry K. Org Lett [Image: see text] A stereocontrolled total synthesis of (+)-chamuvarinin, isolated from the root extract of Uvaria Chamae, utilizes a convergent modular strategy to construct the adjacently linked C15−C28 ether array, followed by a late-stage Julia−Kocienski olefination to append the butenolide motif. This constitutes the first total synthesis of (+)-chamuvarinin, defining the relative and absolute configuration of this unique annonaceous acetogenin. American Chemical Society 2010-12-21 2011-02-04 /pmc/articles/PMC3031177/ /pubmed/21174397 http://dx.doi.org/10.1021/ol1028699 Text en Copyright © 2010 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org. |
| spellingShingle | Florence, Gordon J. Morris, Joanne C. Murray, Ross G. Osler, Jonathan D. Reddy, Vanga R. Smith, Terry K. Synthesis and Stereochemical Assignment of (+)-Chamuvarinin |
| title | Synthesis and Stereochemical Assignment of (+)-Chamuvarinin |
| title_full | Synthesis and Stereochemical Assignment of (+)-Chamuvarinin |
| title_fullStr | Synthesis and Stereochemical Assignment of (+)-Chamuvarinin |
| title_full_unstemmed | Synthesis and Stereochemical Assignment of (+)-Chamuvarinin |
| title_short | Synthesis and Stereochemical Assignment of (+)-Chamuvarinin |
| title_sort | synthesis and stereochemical assignment of (+)-chamuvarinin |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3031177/ https://www.ncbi.nlm.nih.gov/pubmed/21174397 http://dx.doi.org/10.1021/ol1028699 |
| work_keys_str_mv | AT florencegordonj synthesisandstereochemicalassignmentofchamuvarinin AT morrisjoannec synthesisandstereochemicalassignmentofchamuvarinin AT murrayrossg synthesisandstereochemicalassignmentofchamuvarinin AT oslerjonathand synthesisandstereochemicalassignmentofchamuvarinin AT reddyvangar synthesisandstereochemicalassignmentofchamuvarinin AT smithterryk synthesisandstereochemicalassignmentofchamuvarinin |