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An efficient synthesis of 1α, 25-dihydroxy vitamin D3

✍ Scribed by L. Vanmaele; P.J. De Clercq; M. Vandewalle

Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
284 KB
Volume
41
Category
Article
ISSN
0040-4020

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✦ Synopsis

An efficient synthesis of the title compound is reported based on C-l functionalization of the triazoline Diels-Alder adduct of 25-OH previtamin D3 (2). lu,25-Dihydroxy vitamin D3 (la) is considered as the most important and active natural metabolite of vitamin D 1 3 -Recently we have described a novel synthesis2 of the la-hydroxy vitamin D3 analogue (g), via a route essentially based on the C-l functionalization of a previtamin D3 derivative (2b) in which the unstable triene system is protected as a Diels-Alder adduct (cf. 3). We now report the application of this general plan to the synthesis of the title compound3. Treatment of crude 25-hydroxy previtamin D3 (z)(obtained upon low temperature irradiation of 25-hydroxy-7-dehydrocholesterol with a high-pressure Hg-lamp) 4 with phenyl-1,2,4-triazoline-3,5-dione in CH2C12 led with complete regio-and stereoselectivity (9 attack) to the adduct 2 in 49 % yield. After selective protection of the 3-hydroxyl function as the tert-butyldimethylsilyl ether (4; 92 % yield), allylic bromination with 1,3-dibromo-5,5-dimethylhydantoin in hexane-CH2C12 (collidine, AIBN, 20 min reflux) led with high regioselectivity to the diastereoisomeric bromides at C-l (crude yield > 80 %). Immediate oxidation of the allylic bromides with bis-tetrabutyl-ammoniumdichromate 5

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