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Studies on the synthesis of side chain hydroxylated metabolites of vitamin D. Stereospecific syntheses of 25-hydroxy-7,8-dihydroergosterol and its C-24 epimer

✍ Scribed by F.J. Sardina; A. Mouriño; L. Castedo

Book ID
104219908
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
214 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

An efficient, stereospecific synthesis of 25-hydroxy-7,8-dihydroerqosterol, starting from the aldehyde 3 (7 steps, 30,: overally was developed. Key steps are the stereospecific displacement of an allylic carbamate by

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Stereospecific synthesis of hydroxylated
Stereospecific synthesis of hydroxylated steroid side chains. Synthesis of 25,28-dihydroxy-7,8-dihydroergosterol and its c-24 epimer via [2,3] sigmatropic rearrangement.
✍ M.Mark Midland; Young C. Kwon 📂 Article 📅 1985 🏛 Elsevier Science 🌐 French ⚖ 205 KB

LiCzCC(CH3)20TBDMS (t-butyldimethylsilyl) to the aldehyde gave two isomers (4 and 5) in a 1:l ratio. At this point the two C-22 epimers were separated by chromatography in order to achieve the stereospecifit synthesis of the two C-24 epimers. The less polar isomer was assigned as the (22R)-steroid 4