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Synlett 1995; 1995(8): 857-858
DOI: 10.1055/s-1995-5097
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Enantioselective Synthesis of a Bicyclo[3.1.0]hexane A-Ring Synthon for 1α, 25-Dihydroxyvitamin D3

William G. Dauben* , Timothy A. Lewis
  • *Department of Chemistry, University of California, Berkeley, California 94720-1460, USA
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Publication Date:
31 December 2000 (online)

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A bicyclo[3.1.0]hexane A-ring synthon of 1α, 25-dihydroxyvitamin D3 has been prepared starting with (S)-malic acid. The key step in the sequence involves a highly diastereoselective intermolecular cyclopropanation reaction of a chiral cyclopentenone. This method avoids using a selenium oxidation to introduce the 1α-hydroxy group.

1α, 25-dihydroxyvitamin D3 - diastereoselective cyclopropanation - malic acid - chiral cyclopentenone

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