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 inJournal of organic chemistry Vol. 78; no. 23; pp. 11807 - 11814
Main Authors Nicolas, Lionel, Izquierdo, Eva, Angibaud, Patrick, Stansfield, Ian, Meerpoel, Lieven, Reymond, Sébastien, Cossy, Janine
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.12.2013
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Cobalt - chemistry
Furans - chemical synthesis
Furans - chemistry
Molecular Conformation
Organometallic Compounds - chemistry
Physical Sciences
Pyrones - chemistry
Science & Technology
GLYCOSIDES
(+)-ALTHOLACTONE
ALKYL
DNA
NUCLEOSIDES
ARYL
CROSS-COUPLING APPROACH
STEREOSELECTIVE-SYNTHESIS
ENANTIOSELECTIVE TOTAL-SYNTHESIS
ISOALTHOLACTONE
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401845q