85639-62-9Relevant articles and documents
Further studies on the synthesis of 24(S),25-epoxycholesterol. A new, efficient preparation of desmosterol
Spencer, Thomas A.,Li, Dansu,Russel, Jonathon S.,Tomkinson, Nicholas C. O.,Willson, Timothy M.
, p. 1919 - 1923 (2007/10/03)
Efforts to improve the synthesis of 24(S),25-epoxycholesterol (1) from stigmasterol (3) have included identification of 6α-hydroxy-i-steroid 11 as a byproduct from the ozonolysis of 9 and an attempt to effect conversion of sulfone 14 to diol 18 via Payne rearrangement and nucleophilic trapping of epoxide 25, which led instead to 27 and 28 (97% yield). A more efficient synthesis of 1 was achieved via coupling of cuprate 21 with allylic acetate 31 to give 73% of 16, in the most efficient conversion yet of a C22 intermediate to desmosterol (5) or its acetate 6.
Stereoselective Synthesis of Squalamine Dessulfate
Moriarty, Robert M.,Enache, Livia A.,Kinney, William A.,Allen, Craig S.,Canary, James W.,et al.
, p. 5139 - 5142 (2007/10/02)
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
