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Further studies on synthesis of 24(S),25-epoxycholesterol : new efficient preparation of desmosterol

Spencer Thomas A., Jr. and Li, Dansu and Russel, Jonathon S. and Tomkinson, Nicholas C. O. and Willson, Timothy M. (2000) Further studies on synthesis of 24(S),25-epoxycholesterol : new efficient preparation of desmosterol. In: 219th Meeting of the American Chemical Society, 2000-03-26 - 2000-03-30.

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Abstract

Our synthesis of the regulatory oxysterol 24(S),25-epoxycholesterol (1) from stigmasterol has been improved by the discovery that cuprate 2 can be coupled with allylic acetate 3 to give in 73% yield in the key step of the most effecient conversion yet of a C22 intermediate to desmosteryl acetate (4). Efforts to prep. diol 5 from sulfone 6 via Payne rearrangement of epoxide 7 will also be presented. [on SciFinder(R)]