✦ LIBER ✦
Steroids and sex hormons. Part 264. Lewis acid catalyzed reversible [1,5]-hydride shift in 3,19-epoxy-steroids
✍ Scribed by Georg Acklin; Walter Graf
- Book ID
- 102859059
- Publisher
- John Wiley and Sons
- Year
- 1980
- Tongue
- German
- Weight
- 913 KB
- Volume
- 63
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
3β, 19‐Epoxy‐3 α‐methoxy‐steroids (e.g. 1, Scheme 1) are converted into the corresponding 3 α‐methoxy‐19‐oxo compounds (e.g. 3) in the presence of boron trifluoride etherate, via an intramolecular hydride ion transfer from C (19) to (3) which is shown to be an equilibrium process. By subjecting the specifically deuteriated (19 S)‐ and (19 R)‐compounds 1b and 1c to this reaction it was shown to be highly stereoselective.