Regio- and stereospecific synthesis of dl-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol

Latif Kelebekli,Kadir Aksu,Ertan Şahin

doi:10.1016/j.tetlet.2018.02.050

Regio- and stereospecific synthesis of dl-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol

Latif Kelebekli, Kadir Aksu + Show 1 more

https://doi.org/10.1016/j.tetlet.2018.02.050

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Journal: Tetrahedron Letters	Publication Date: Feb 21, 2018
Citations: 5

Affiliation: Ordu University, Atatürk University

#Regiospecific Bromination #Alkene Moiety + Show 3 more

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Abstract

The regio- and stereospecific synthesis of dl-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol is reported. Bromination of p-benzoquinone followed by reduction of the carbonyl groups with NaBH4 gave the corresponding trans-dibromodiol compound, which was reacted with sodium methoxide to produce dimethoxy conduritol-B. Regiospecific bromination of the alkene moiety furnished the desired chiro-inositol derivative.

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