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Synlett 1995; 1995(10): 1063-1064
DOI: 10.1055/s-1995-5162
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The Synthesis of 10,19-Dihydro-10-methyl 1α,25-Dihydroxyvitamin D3

Bruno Linclau, Maurits Vandewalle*
  • *University of Gent, Department of Organic Chemistry, Laboratory for Organic Synthesis, Krijgslaan, 281 (S.4), B-9000 GENT (Belgium)
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Publication Date:
31 December 2000 (online)

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The title compound is constructed via Lythgoe’s procedure. The crucial steps towards the ”A-ring” phosphine oxide precursor 5 involve (i) elaboration of the 1,3-trans diol configuration, via stereoselective epoxidation of 8 and (ii) the introduction of the Z-substituted double bond via a highly selective selenation-oxidation-elimination procedure on ester 14.

substituted 1,3-trans cyclohexanediol - allylic diphenyl phosphine oxide - stereoselective epoxidation - stereoselective selenation

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