A highly stereoselective synthesis of C-24 and C-25 oxysterols from desmosterol
A new highly stereoselective construction of the side chain of the C-24 and C-25 oxysterols has been achieved by using desmosterol acetate as the starting material and an improved Sharpless catalytic asymmetric dihydroxylation with 100% d.e. (diastereomeric excess) as the key step. The result is much better than the usual asymmetric dihydroxylation procedure. t-Butyl nitrite/2,2,6,6-tetramethylpiperidine N-oxyl radical/FeCl3 catalyst system was developed to activate molecular oxygen for the aerobic oxidation of 24-hydroxycholesterol and the 24-ketocholesterol was obtained in 86.2% yield. The oxidation system has never been reported before. The mechanism for the catalytic aerobic oxidation was also proposed.
Stereoselective Synthesis of Squalamine Dessulfate
Squalamine dessulfate (24R) and the unnatural product squalamine dessulfate (24S) have been synthesized from stigmasterol.The key step is establishing the C24 stereochemistry is attachment of the sidechain at C22 using either (2R)- or (2S)-1,2-epoxy-3-met
Moriarty, Robert M.,Enache, Livia A.,Kinney, William A.,Allen, Craig S.,Canary, James W.,et al.
p. 5139 - 5142
(2007/10/02)
A Stereoselective Synthesis and a Convenient Synthesis of Optically Pure (24 R)- and (24 S)-24-hydroxycholesterols
A new stereoselective synthesis of optically pure (24 S)-24-hydroxycholesterol (cerebrosterol) and (24 R)-24-hydroxycholesterol, using D- and L-valines as chiral sources, as well as a convenient synthesis, are described.
Koch, Patrick,Nakatani, Yoichi,Luu, Bang,Ourisson, Guy
p. 185 - 194
(2007/10/02)
Stereoselective Synthesis of (22R)- and (22S)-22-Methylcholesterol
22-Methylcholesterol, though hitherto unknown, is likely to exist in nature in the marine environment.In order to facilitate its eventual recognition, stereoselective syntheses of the 22R and 22S isomers of 22-methylcholesterol were developed by using the
Zielinski, Jan,Li, Hui-ting,Djerassi, Carl
p. 620 - 625
(2007/10/02)
Chirality Transfer in the Cholesterol Side Chain; Synthesis of (24R)- and (24S)-24-Hydroxycholesterols
Δ23-22-Acetoxycholesterol derivatives can be converted into 24-hydroxycholesterol derivatives highly stereoselectively by 1,3-chirality transfer with bis(acetonitrile)palladium(II) dichloride.
Takatsuto, Suguru,Ishiguro, Masaji,Ikekawa, Nobuo
p. 258 - 260
(2007/10/02)
Absolute configurations of 24 hydroxycholesterol and related compounds
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Koizumi,Morisaki,Ikekawa,et al.
p. 2203 - 2206
(2007/10/12)
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