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Synlett 1995; 1995(10): 1063-1064
DOI: 10.1055/s-1995-5162
DOI: 10.1055/s-1995-5162
letter
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The Synthesis of 10,19-Dihydro-10-methyl 1α,25-Dihydroxyvitamin D3
Further Information
Publication History
Publication Date:
31 December 2000 (online)
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