Synthesis of C-19-Functionalized 1α-Hydroxyvitamin D2 Analogues via Ring-Closing Metathesis

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A heteroatom-tethered regioselective ring-closing metathesis reaction was used for the C-19 functionalization of 1alpha-hydroxy-5,6-trans-vitamin D(2) analogues. Applications of the reaction to form a range of analogues by manipulation of the tether using both organolithium reagents and Diels-Alder cycloadditions are described.