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Synthesis 1989; 1989(2): 93-97
DOI: 10.1055/s-1989-27161
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Stereoselective Synthesis of Cholesteryl Derivatives Bearing a Chiral Allenic Group in the Side Chain

Alain Burger* , Charles Hetru, Bang Luu
  • *Laboratoire de Chimie Organique des Substances Naturelles UA 31, CNRS, 5 rue Blaise Pascal, F-67084 Strasbourg, France
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Publication Date:
17 September 2002 (online)

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Two cholesteryl allenic stereoisomers (aS)-11 and (aR)-11 are prepared stereoselectively. The key step of the synthesis is the coupling of pregnenolone to the lithium salt of the optically active 5-ethynyl-1,3-dioxolane (S)-8 or (R)-8. These two chiral synthons are obtained from the enantiomer primary alcohol (S)-3 and (R)-3, which are prepared according to a new synthetic pathway from methyl (2S)- and (2R)-2,3-O-isopropylideneglycerate [(S)-1 and (R)-1].