Efficient routes to epimerically-pure side-chain derivatives of lanosterol
Kavtaradze, L.K., Manley-Harris, M. & Nicholson, B.K. (2004). Efficient routes to epimerically-pure side-chain derivatives of lanosterol. Steroids, 69, 227-233.
Permanent Research Commons link: https://hdl.handle.net/10289/189
A technically simple route is described to individual epimers of side-chain derivatives of lanosterol (3-hydroxy-5-lanosta-8,24-diene). Epimerically pure 24,25-epoxy-, 24,25-dihydroxy- and 24-bromo-25-hydroxy-lanosterol have been prepared in good yield from commercial (50-60%) lanosterol. Hypophosphorous acid was used as a catalyst for the cohalogenation of the 24(25) bond and also for the efficient conversion of 24,25-epoxy- and 24-bromo-25-hydroxylanosterol to epimerically pure 24(R) or 24(S)-24,25-dihydroxylanosterols.
This is an authors version of an article published in the journal, Steroids, (c) 2004 Elsevier Inc.