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Stereocontrolled synthesis of (20S)-steroidal side chain

✍ Scribed by Dauben, William G.; Brookhart, Todd

Book ID
126438984
Publisher
American Chemical Society
Year
1982
Tongue
English
Weight
423 KB
Volume
47
Category
Article
ISSN
0022-3263

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Regio and stereochemically controlled ring opening of epoxides with grignard reagents. Stereocontrolled synthesis of the steroid side chains. first stereoselective hemisynthesis of 20s isolanosterol.
✍ J.R. Schauder; A. Krief πŸ“‚ Article πŸ“… 1982 πŸ› Elsevier Science 🌐 French βš– 255 KB

This epoxide was obtained stereoselectively (> 95% ) on reaction of corresponding C-2O,C-22 olefin with osmium tetroxide (1.2 eq., 10Β°,1hr,85X yield) followed by basic cyclisation of the resulting C-2O,C-22 diol via its C-22 monomesylate (74% overall yield).