A concise and stereospecific synthesis of some cyclitols containing eight-membered rings: cyclooctane-1,2,3,4-tetraoles

Salamci E.

TETRAHEDRON, cilt.66, sa.23, ss.4010-4015, 2010 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 66 Sayı: 23
  • Basım Tarihi: 2010
  • Doi Numarası: 10.1016/j.tet.2010.04.052
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.4010-4015
  • Anahtar Kelimeler: Cyclitol, Cyclooctanetetraol, Epoxide, Endoperoxide, Synthesis, CLOSING METATHESIS, CARBASUGAR ANALOGS, PROTO-QUERCITOL, DL-PROTO, GLYCOSIDASES, DERIVATIVES, INHIBITORS, POLYOLS, POLYCYCLITOLS, ENDOPEROXIDES
  • Atatürk Üniversitesi Adresli: Evet

Özet

A concise and efficient synthesis of cyclooctane-1,2,3,4-tetraoles, new polyhydroxylated eight-membered carbocycles, is described starting from cis,cis-1,3-cyclooctadiene. Cyclooctene endoperoxide obtained by photooxygenation of cis,cis-1,3-cyclooctadiene was the key compound in the synthesis. Reduction of the endoperoxide with zinc or thiourea followed by acetylation of the hydroxyl group and OsO4/NMO oxidation of the double bond gave (1R(S),2S(R),3R(S),4S(R))-cyclooctane-1,2,3,4-tetraol. Interestingly, epoxidation of cyclooctene-1,4-diol with m-CPBA also afforded trans-epoxy-diol 17. (1R(S),2R(S),3R(S),4S (R))-cyclooctane-1,2,3,4-tetraol was easily obtained by hydrolysis of epoxy-diol 17. (C) 2010 Elsevier Ltd. All rights reserved.