Synthese von 5α-Androstan-3β,14β,17β-triol
✍ Scribed by Gerd Schubert; Dieter Tresselt; Manfred Wunderwald
- Publisher
- Wiley (John Wiley & Sons)
- Year
- 2010
- Weight
- 138 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0044-2402
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**Synthesis of 5β‐Androstane‐3,17‐dione from Cholic Acid** An efficient synthesis of 5β‐androstane‐3,17‐dione (**4**) from cholic acid is presented. Key step is the photochemical side‐chain degradation of a suitable bile acid derivative (**1**).
The ring conformation of the title compound, C 19 H 30 O 3 , is similar to that of the 5-epimer except for the cis A/B ring junction. Ring D adopts a 13,14-half chair conformation. The molecules are linked together by a two-dimensional network of hydrogen bonds involving the carbonyl and hydroxyl gr
## Abstract The synthesis of A‐nor‐5β‐androstane‐2α,5,17β‐triol (**8**), A‐nor‐5β‐androstane‐2β,5,17β‐triol (**10**), A‐nor‐5α‐androstane‐2β,5,17β‐triol (**20**), A‐nor‐5α‐androstane‐2β,5,17β‐triol (**22**) and of their 17‐O‐benzoyl derivatives is described, using A‐nor‐testosterone (**1**) as star