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Open Access research with a European policy impact...

The Strathprints institutional repository is a digital archive of University of Strathclyde's Open Access research outputs. Strathprints provides access to thousands of Open Access research papers by Strathclyde researchers, including by researchers from the European Policies Research Centre (EPRC).

EPRC is a leading institute in Europe for comparative research on public policy, with a particular focus on regional development policies. Spanning 30 European countries, EPRC research programmes have a strong emphasis on applied research and knowledge exchange, including the provision of policy advice to EU institutions and national and sub-national government authorities throughout Europe.

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

Spencer, Thomas A. and Li, Dansu and Russel, Jonathon S. and Tomkinson, Nicholas C. O. and Willson, Timothy M. (2000) Further studies on the synthesis of 24(S),25-epoxycholesterol. A new, efficient preparation of desmosterol. Journal of Organic Chemistry, 65 (7). pp. 1919-1923. ISSN 0022-3263

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Abstract

Efforts to improve the synthesis of 24(S),25-epoxycholesterol from stigmasterol have included identification of 6α-hydroxy-i-steroid (I) (R1 = OH, R2 = αOH) as a byproduct from the ozonolysis of steroid (II) and an attempt to effect conversion of sulfone I (R1 = SO2Ph, R2 = βOMe) (III) to diol (IV) via Payne rearrangement and nucleophilic trapping of (S)-2-hydroxymethyl-3,3-dimethylepoxide, which led instead to (V) (R3 = α or β OH) (97% yield). A more efficient synthesis of 24(S),25-epoxycholesterol was achieved via coupling of cuprate I (R1 = CuCNLi, R2 = βOMe) (VI) with allylic acetate H2C=CHCMe2OAc to give 73% of I (R1 = CH2CH=CMe2, R2 = βOMe) (VII), in the most efficient conversion yet of a C22 intermediate to desmosterol or its acetate.