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Stereoselective Convergent Synthesis of 24,25-Dihydroxyvitamin D3 Metabolites: A Practical Approach

✍ Scribed by José Pérez Sestelo; Iván Cornella; Olga de Uña; Antonio Mouriño; Luis A. Sarandeses

Publisher: John Wiley and Sons
Year: 2002
Tongue: English
Weight: 143 KB
Volume: 8
Category: Article
ISSN: 0947-6539
DOI: 10.1002/1521-3765(20020617)8:12<2747::aid-chem2747>3.0.co;2-j

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✦ Synopsis

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.

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