Synthesis of the first 24-aminovitamin D3 derivatives by diastereoselective conjugate addition to a chiral methyleneoxazolidinone in aqueous media.

Pérez Sestelo, J.; de Uña, O.; Mouriño, A.; Sarandeses, L. A.


Synlett 2002, 719–722 (DOI: 10.1055/s-2002-25339).

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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-1a,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 a methyleneoxazolidinone in aqueous media. The conjugate vitamin D triene system was constructed using the Lythgoe approach.