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Synthesis 2003(10): 1500-1502
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

Arif Barana, Hasan Seçen*a, Metin Balci*b
a Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey
b Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey
Fax: +90(312)2101280; e-Mail: mbalci@metu.edu.tr; e-Mail: hsecen@atauni.edu.tr;
Further Information

Publication History

Received 28 February 2003
Publication Date:
08 July 2003 (online)

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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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