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Synthesis 1987; 1987(8): 696-700
DOI: 10.1055/s-1987-28048
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A Novel Stereospecific Synthesis of 22-Hydroxylated Triterpenes and Steroids: Syntheses of 22R-Hydroxylanosterol and 22R-Hydroxydesmosterol

Alain Amann* , Guy Ourisson, Bang Luu
  • *Laboratoire de Chimie Organique des Substances Naturelles U A 31, Centre de Neurochimie, 5 rue Blaise Pascal, F-67084 Strasbourg, France
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Publication Date:
12 September 2002 (online)

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22R-Hydroxylanosterol (10) is prepared from lanosterol (1) with an overall yield of over 30%. The key step of the synthesis is the stereospecific coupling of the aldehyde 7 with an arsenic ylide. The same reaction is used to build the side chain of 22R-hydroxydesmosterol (14).

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