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The Daphniphyllum Alkaloids: Total Synthesis of (−)-Calyciphylline N
[Image: see text] Presented here is a full account on the development of a strategy culminating in the first total synthesis of the architecturally complex daphniphyllum alkaloid, (−)-calyciphylline N. Highlights of the approach include a highly diastereoselective, intramolecular Diels–Alder reactio...
| Autores principales: | , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical
Society
2015
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4394112/ https://www.ncbi.nlm.nih.gov/pubmed/25756504 http://dx.doi.org/10.1021/ja503899t |
| _version_ | 1782366251467669504 |
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| author | Shvartsbart, Artem Smith, Amos B. |
| author_facet | Shvartsbart, Artem Smith, Amos B. |
| author_sort | Shvartsbart, Artem |
| collection | PubMed |
| description | [Image: see text] Presented here is a full account on the development of a strategy culminating in the first total synthesis of the architecturally complex daphniphyllum alkaloid, (−)-calyciphylline N. Highlights of the approach include a highly diastereoselective, intramolecular Diels–Alder reaction of a silicon-tethered acrylate; an efficient Stille carbonylation of a sterically encumbered vinyl triflate; a one-pot Nazarov cyclization/proto-desilylation sequence; and the chemoselective hydrogenation of a fully substituted diene ester. |
| format | Online Article Text |
| id | pubmed-4394112 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2015 |
| publisher | American Chemical
Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-43941122016-03-10 The Daphniphyllum Alkaloids: Total Synthesis of (−)-Calyciphylline N Shvartsbart, Artem Smith, Amos B. J Am Chem Soc [Image: see text] Presented here is a full account on the development of a strategy culminating in the first total synthesis of the architecturally complex daphniphyllum alkaloid, (−)-calyciphylline N. Highlights of the approach include a highly diastereoselective, intramolecular Diels–Alder reaction of a silicon-tethered acrylate; an efficient Stille carbonylation of a sterically encumbered vinyl triflate; a one-pot Nazarov cyclization/proto-desilylation sequence; and the chemoselective hydrogenation of a fully substituted diene ester. American Chemical Society 2015-03-10 2015-03-18 /pmc/articles/PMC4394112/ /pubmed/25756504 http://dx.doi.org/10.1021/ja503899t Text en Copyright © 2015 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
| spellingShingle | Shvartsbart, Artem Smith, Amos B. The Daphniphyllum Alkaloids: Total Synthesis of (−)-Calyciphylline N |
| title | The Daphniphyllum
Alkaloids: Total Synthesis of (−)-Calyciphylline
N |
| title_full | The Daphniphyllum
Alkaloids: Total Synthesis of (−)-Calyciphylline
N |
| title_fullStr | The Daphniphyllum
Alkaloids: Total Synthesis of (−)-Calyciphylline
N |
| title_full_unstemmed | The Daphniphyllum
Alkaloids: Total Synthesis of (−)-Calyciphylline
N |
| title_short | The Daphniphyllum
Alkaloids: Total Synthesis of (−)-Calyciphylline
N |
| title_sort | daphniphyllum
alkaloids: total synthesis of (−)-calyciphylline
n |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4394112/ https://www.ncbi.nlm.nih.gov/pubmed/25756504 http://dx.doi.org/10.1021/ja503899t |
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