A novel and short synthesis of (1,4/2)-cyclohex-5-ene-triol and its conversion to (+/-)-proto-quercitol

Gultekin M., Salamci E., Balci M.

CARBOHYDRATE RESEARCH, cilt.338, sa.16, ss.1615-1619, 2003 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 338 Sayı: 16
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1016/s0008-6215(03)00256-8
  • Dergi Adı: CARBOHYDRATE RESEARCH
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1615-1619
  • Anahtar Kelimeler: quercitol, singlet oxygen, ene-reaction, endoperoxide, hydroperoxide, DL-PROTO-QUERCITOL, DIASTEREOSELECTIVE ENE REACTION, SINGLET OXYGEN, CONVENIENT SYNTHESIS, INOSITOL, CONDURITOLS, CONCISE
  • Orta Doğu Teknik Üniversitesi Adresli: Hayır

Özet

(1,4/2)-Cyclohex-5-ene-triol was synthesized starting from cyclohexa-1,4-diene with two different approaches. Photooxygenation of cyclohexa-1,4-diene and epoxy-cyclohexene afforded anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide and anti-7-oxabicclo[4.1.0]hept-4-en-3-yl hydroperoxide, respectively. Hydroperoxy endoperoxide was reduced with aqueous sodium bisulfite; hydroperoxy-epoxide with dimethylsulfide-titanium tetraisopropoxide to give 7-oxabicyclo[4.1.0]hept-4-en-3-ol. Acidic hydrolysis of the epoxy-alcohol gave the (1,4/2)-cyclohex-3-ene-triol. Oxidation of the double bond with KMnO4 resulted in the formation of proto-quercitol. (C) 2003 Elsevier Ltd. All rights reserved.