Stereoselective convergent synthesis of 24,25-dihydroxyvitamin D3 metabolites: a practical approach.
Vitamin D3 active metabolites 24R,25-(OH)2-D3, 24S,25-(OH)2-D3, and 1 alpha, 24R,25-(OH)3-D3 were synthesized by a convergent and stereoselective approach. In the synthetic route, the stereogenic center at C-24 was generated through ultrasonically induced aqueous conjugate addition of iodide 6 to Seebach's dioxolanone 5, and the vitamin D triene system was constructed using the Lythgoe approach. The synthesis, which is both short (seven steps from iodide 6) and efficient (32-40% overall yield), allows the preparation of large quantities of the metabolites and provides a novel example of a highly stereoselective reaction promoted by the zinc-copper couple in aqueous media.
Pérez Sestelo
José
J
Departamento de Química Fundamental Universidade da Coruña, 15071 A Coruña, Spain.
Cornella
Iván
I
de Uña
Olga
O
Mouriño
Antonio
A
Sarandeses
Luis A
LA
D015650:24,25-Dihydroxyvitamin D 3 / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D015650:24,25-Dihydroxyvitamin D 3