- Calciferol and its Relatives. Part 28. A Stereoselective Synthesis of 1α-Hydroxyprecalciferol3 from 8-Hydroxymethyl-des-AB-cholest-8-ene
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8-p-Tolylsulphonylmethyl-des-AB-cholest-8-ene (1) and methyl (3S,5R)-3,5-bis-t-butyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate (2) were combined to give a 6-oxo-7-sulphone from which 1α,3β-diacetoxy-9,10-seco-cholesta-5(10),8-diene-6-yne (4) was obtained.Semihydrogenation and deacetylation gave 1α-hydroxyprecalciferol3 (6), which was converted by thermal isomerization into 1α-hydroxyvitamin D3 (7).
- Lithgoe, Basil,Waterhouse, Ian
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p. 1405 - 1406
(2007/10/02)
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