Cobalt-Catalyzed Diastereoselective Synthesis of C‑Furanosides. Total Synthesis of (−)-Isoaltholactone

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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Veröffentlicht in:Journal of organic chemistry 2013-12, Vol.78 (23), p.11807-11814
Hauptverfasser: Nicolas, Lionel, Izquierdo, Eva, Angibaud, Patrick, Stansfield, Ian, Meerpoel, Lieven, Reymond, Sébastien, Cossy, Janine
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cobalt - chemistry
Furans - chemical synthesis
Furans - chemistry
Molecular Conformation
Organometallic Compounds - chemistry
Pyrones - chemistry
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401845q