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Synlett 2010(16): 2392-2396
DOI: 10.1055/s-0030-1258560
DOI: 10.1055/s-0030-1258560
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Spiro C-Arylglycoriboside via Pd(II)-Catalyzed Spirocyclization
Weitere Informationen
Received
10 June 2010
Publikationsdatum:
03. September 2010 (online)
Publikationsverlauf
Publikationsdatum:
03. September 2010 (online)
![](https://www.thieme-connect.de/media/synlett/201016/lookinside/thumbnails/10.1055-s-0030-1258560-1.jpg)
Abstract
Spiro C-arylglycoriboside was synthesized in 21 steps via Pd(II)-catalyzed spirocyclization as a key reaction. Hemiketal was obtained in 47% overall yield from cis-2-butene-1,4-diol and spirocyclized with PdCl2(PhCN)2 in dilute THF solution (0.01 M) to afford the 1,6-dioxaspiro[4.4]nonane skeleton in high yield. The spirocyclo adduct was transformed into spiro C-arylglycoriboside in five steps.
Key words
spiro compound - palladium - heterocycles - stereoselectivity - cyclization
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References and Notes
The stereochemistry of 10a was confirmed unequivocally by single-crystal X-ray diffraction analysis.