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Synlett 1993; 1993(8): 609-610
DOI: 10.1055/s-1993-22550
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An Efficient and Stereospecific Synthesis of proto-Quercitol

Hasan Seçen* , Emine Salamci, Yaşar Sütbeyaz, Metin Balci
  • *Atatürk University, Department of Chemistry, 25240 Erzurum, Turkey
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Publication Date:
19 March 2002 (online)

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A new and stereospecific synthesis for DL-proto-quercitol has been developed starting from commercial 1,4-cyclohexadiene. Photooxygenation of 1 resulted in the formation of 3 whose configuration has been determined from spectroscopic data and by chemical interconversions. LiAlH4 or thiourea reduction of the peroxide linkages in 3 gave cyclohexenetriol 4a. KMnO4 oxidation of the corresponding cyclohexene acetate 4b followed by ammonolysis gave 6a as the sole product in high yield.