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Synthesis 2003(10): 1500-1502
DOI: 10.1055/s-2003-40517
DOI: 10.1055/s-2003-40517
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York
An Efficient and Highly Stereoselective Synthesis of gala-Quercitol from 1,4-Cyclohexadiene
Further Information
Received
28 February 2003
Publication Date:
08 July 2003 (online)
Publication History
Publication Date:
08 July 2003 (online)
Abstract
gala-Quercitol was synthesized from 1,4-cyclohexadiene in seven steps and overall yield of 68%. Reaction of 5,6-dibromo-2,2-dimethylhexahydro-1,3-benzodioxole, synthesized from 1,4-cyclohexadiene in three steps, with excess NaOMe gave (3aα,5α,7aα)-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole. cis-Hydroxylation of the benzodioxole followed by acetylation with AcCl gave 5-O-methyl-gala-quercitol tetraacetate from which gala-quercitol was obtained by hydrolysis and demethylation with aq HBr (47%).
Key words
alcohols - quercitol - cyclohexol - cyclitol - hydroxylation - eliminations - stereoselective synthesis
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