Abstract
The synthesis of the first 24-aminovitamin D3 derivatives is reported. A stereoselective convergent synthetic approach was employed to prepare 24(S)-benzoylamino-25-hydroxyvitamin D3 and 24(S)-benzoylamino-1α,25-dihydroxyvitamin D3 in six steps from iodide 2 in 34% and 42% overall yields, respectively. The key step in the synthesis is a novel diastereoselective ultrasonically induced conjugate addition, promoted by the zinc-copper couple, of iodide 2 to methyleneoxazolidinone 4 in aqueous media. The conjugate vitamin D triene system was constructed using the Lythgoe approach.
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