An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene

Date

2003-07-01

Author

Baran, A
Secen, H
Balcı, Metin

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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 (3aalpha,5alpha,7aalpha)-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%).

Subject Keywords

Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/56784

Journal

SYNTHESIS-STUTTGART

DOI

https://doi.org/10.1055/s-2003-40517

Collections

Graduate School of Natural and Applied Sciences, Article

Citation Formats

A. Baran, H. Secen, and M. Balcı, “An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene,” SYNTHESIS-STUTTGART, no. 10, pp. 1500–1502, 2003, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56784.