Cobalt-Catalyzed Diastereoselective Synthesis of C‑Furanosides. Total Synthesis of (−)-Isoaltholactone
An array of C-aryl and C-vinyl furanosides were prepared in good yields and diastereoselectivities from C-halogeno furanosides either with aryl Grignard or with vinyl Grignard using the convenient Co(acac)3/TMEDA catalytic system. This method is illustrated by the total synthesis of the (−)-isoaltho...
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| Published in | Journal of organic chemistry Vol. 78; no. 23; pp. 11807 - 11814 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
06.12.2013
Amer Chemical Soc |
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| Online Access | Get full text |
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| Abstract | An array of C-aryl and C-vinyl furanosides were prepared in good yields and diastereoselectivities from C-halogeno furanosides either with aryl Grignard or with vinyl Grignard using the convenient Co(acac)3/TMEDA catalytic system. This method is illustrated by the total synthesis of the (−)-isoaltholactone. |
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| AbstractList | An array of C-aryl and C-vinyl furanosides were prepared in good yields and diastereoselectivities from C-halogeno furanosides either with aryl Grignard or with vinyl Grignard using the convenient Co(acac)3/TMEDA catalytic system. This method is illustrated by the total synthesis of the (-)-isoaltholactone. An array of C-aryl and C-vinyl furanosides were prepared in good yields and diastereoselectivities from C-halogeno furanosides either with aryl Grignard or with vinyl Grignard using the convenient Co(acac)3/TMEDA catalytic system. This method is illustrated by the total synthesis of the (−)-isoaltholactone. |
| Author | Meerpoel, Lieven Angibaud, Patrick Nicolas, Lionel Izquierdo, Eva Cossy, Janine Stansfield, Ian Reymond, Sébastien |
| AuthorAffiliation | Janssen-Cilag Laboratoire de Chimie Organique Janssen Research & Development ESPCI ParisTech, UMR CNRS 7084 Janssen Pharmaceutica N.V |
| AuthorAffiliation_xml | – name: ESPCI ParisTech, UMR CNRS 7084 – name: Laboratoire de Chimie Organique – name: Janssen Pharmaceutica N.V – name: Janssen-Cilag – name: Janssen Research & Development |
| Author_xml | – sequence: 1 givenname: Lionel surname: Nicolas fullname: Nicolas, Lionel – sequence: 2 givenname: Eva surname: Izquierdo fullname: Izquierdo, Eva – sequence: 3 givenname: Patrick surname: Angibaud fullname: Angibaud, Patrick – sequence: 4 givenname: Ian surname: Stansfield fullname: Stansfield, Ian – sequence: 5 givenname: Lieven surname: Meerpoel fullname: Meerpoel, Lieven – sequence: 6 givenname: Sébastien surname: Reymond fullname: Reymond, Sébastien email: sebastien.reymond@espci.fr – sequence: 7 givenname: Janine surname: Cossy fullname: Cossy, Janine email: janine.cossy@espci.fr |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24127819$$D View this record in MEDLINE/PubMed |
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| Keywords | GLYCOSIDES (+)-ALTHOLACTONE ALKYL DNA NUCLEOSIDES ARYL CROSS-COUPLING APPROACH STEREOSELECTIVE-SYNTHESIS ENANTIOSELECTIVE TOTAL-SYNTHESIS ISOALTHOLACTONE |
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| Snippet | An array of C-aryl and C-vinyl furanosides were prepared in good yields and diastereoselectivities from C-halogeno furanosides either with aryl Grignard or... |
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| SubjectTerms | Catalysis Chemistry Chemistry, Organic Cobalt - chemistry Furans - chemical synthesis Furans - chemistry Molecular Conformation Organometallic Compounds - chemistry Physical Sciences Pyrones - chemistry Science & Technology |
| Title | Cobalt-Catalyzed Diastereoselective Synthesis of C‑Furanosides. Total Synthesis of (−)-Isoaltholactone |
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