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Synthesis of vitamin D3 and related compounds

✍ Scribed by Tetsuji Kametani; Hiroko Furuyama

Publisher
John Wiley and Sons
Year
1987
Tongue
English
Weight
978 KB
Volume
7
Category
Article
ISSN
0198-6325

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✦ Synopsis

Recently much attention has focused on inducing the hydroxyl group at C-1 and C-25 positions of 1 to obtain the active compound (2, 3, and 4).

A. From Cholesterol

Barton et a1.6 reported in 1973 the convenient synthesis of 1-OH-D3 (3) from la,2a-epoxycholesta-4,6-dien-3-one (8) (obtained from 5 by two steps). Treatment of 8 with large excesses each of lithium metal and ammonium chloride in ammonia-THF under reflux gave la-hydroxycholesterol. Acetylation and subsequent bromination afforded the bromo compound, which was dehydrobrominated to give the diene diacetate (9). After irradiation of 9, the re-

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