A convenient synthesis of [3-3H]squalene and [3-3H]-2,3-oxidosqualene

[3-3H]Squalene and [3-3H]-2,3-oxidosqualene, key compounds for studying the biosynthesis of sterols, were synthesized. The main step was a modified Wittig reaction of [1-3H]trisnorsqualene aldehyde with a phosphorus ylide to give [3-3H]squalene or with a sulfur ylide to give [3-3H]-2,3-oxidosqualene. These compounds were obtained in high radiochemical yield and high purity under simple conditions.

[1]  F. Viola,et al.  2,3-Epoxy-10-aza-10,11-dihydrosqualene, a high-energy intermediate analogue inhibitor of 2,3-oxidosqualene cyclase. , 1992, Journal of medicinal chemistry.

[2]  F. Viola,et al.  Characterization and partial purification of squalene-2,3-oxide cyclase from Saccharomyces cerevisiae. , 1992, Archives of biochemistry and biophysics.

[3]  G. Prestwich,et al.  Regio- and stereo-controlled synthesis of [24,30-14C]-labeled-2,3-epoxysqualene , 1991 .

[4]  H. Williams,et al.  Synthesis of 10,15‐[13C2]‐squalene and ‐DL‐squalene oxide , 1990 .

[5]  F. Viola,et al.  Drug design based on biosynthetic studies: Synthesis, biological activity, and kinetics of new inhibitors of 2,3-oxidosqualene cyclase and squalene epoxidase , 1989, Steroids.

[6]  F. Viola,et al.  Synthesis and biological activity of azasqualenes, bis-azasqualenes and derivatives , 1987 .

[7]  H. DeLuca,et al.  Synthesis and biological activity of 1 alpha-fluoro-25-hydroxyvitamin D3. , 1984, Chemical & pharmaceutical bulletin.

[8]  G. Sandmann,et al.  Enzymatic Preparation of 14C-Labeled Phytoene, Squalene, and Geranylgeranyl Pyrophosphate from [2-14C]Mevalonic Acid , 1980 .

[9]  D. Barton,et al.  Biosynthesis of terpenes and steroids. Part IV. Specific hydride shifts in the biosynthesis of lanosterol and β-amyrin , 1971 .

[10]  J. Biellmann,et al.  Synthèse du squalène et d'analogues , 1971 .

[11]  R. Ratcliffe,et al.  Improved procedure for oxidations with the chromium trioxide-pyridine complex , 1970 .

[12]  R. Hanzlik,et al.  [9] Synthesis of labeled squalene and squalene 2,3-oxide , 1969 .

[13]  E. Corey,et al.  2,3-oxidosqualene, an intermediate in the biological synthesis of sterols from squalene. , 1966, Journal of the American Chemical Society.

[14]  K. K. Mathew,et al.  507. A stereoselective synthesis of squalene , 1959 .

[15]  D. W. Dicker,et al.  407. Synthetical studies on terpenoids. Part I. The synthesis of squalene , 1958 .