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http://hdl.handle.net/11154/2391
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| Title: | Abnormal Beckmann rearrangement in 23-hydroxyiminodiosgenin acetate |
| Authors: | Iglesias-Arteaga, MA
Sandoval-Ramirez, J
Mata-Esma, MY
Vinas-Bravo, O
Bernes, S |
| Issue Date: | 2004 |
| Abstract: | A new transformation of the spiroketal side chain of diosgenin is reported: treatment of 23-hydroxyiminodiosgenin acetate with phosphorous oxychloride in pyridine produced an abnormal Beckmann rearrangement directing to the cleavage of the spiroketal side chain and generating 23,24-bisnorchol-5-enic skeletons: (2'R)-3'-cyano-2'-methylpropyl 3beta-acetoxy-16alpha-chLoro-23,24-bisnorchol-5-en-22-oate as the main product, and small amounts of (2'R)-3'-cyano-2'-methylpropyl 3beta-acetoxy-16alpha-hydroxy-23,24-bisnorchol-5-en-22-oate and vespertilin acetate. (C) 2004 Elsevier Ltd. All rights reserved. |
| URI: | http://hdl.handle.net/11154/2391 |
| ISSN: | 0040-4039 |
| Appears in Collections: | Ciencias
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