Stereoselective conversion of vitamin D3into its 3β-halogenated derivatives. The synthesis of a 1α-hydroxy-3β-fluorovitamin D3analogue

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Abstract
(6R)-Hydroxy-3,5-cyclovitamin D3 was converted with HF, HCl, and HBr into 3β-fluoro-, 3β-chloro-, and 3β-bromo-3-deoxyvitamin D3 respectively, and with NaI–ZnCl2 into the corresponding 3β-iodo derivative; a 3β-fluoro-1α-hydroxyvitamin D3 analogue was prepared from 1α-hydroxyvitamin D3 tosylate using the 3,5-cyclovitamin derivative as an intermediate.