AN EFFICIENT AND STEREOSPECIFIC SYNTHESIS OF PROTO-QUERCITOL

SECEN H., SALAMCI E., SUTBEYAZ Y., BALCI M.

SYNLETT, sa.8, ss.609-610, 1993 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 1993
  • Doi Numarası: 10.1055/s-1993-22550
  • Dergi Adı: SYNLETT
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, EMBASE
  • Sayfa Sayıları: ss.609-610
  • Atatürk Üniversitesi Adresli: Evet

Özet

A new and stereospecific synthesis for DL-proto-quercitol has beeR 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.