Title of article
Abnormal Beckmann rearrangement in 23-hydroxyiminodiosgenin acetate
Author/Authors
Iglesias-Arteaga، نويسنده , , Mart??n A. and Sandoval-Ram??rez، نويسنده , , Jes?s and Mata-Esma، نويسنده , , Marian Y. and Vi?as-Bravo، نويسنده , , Omar and Bernès، نويسنده , , Sylvain، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2004
Pages
6
From page
4921
To page
4926
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 3β-acetoxy-16α-chloro-23,24-bisnorchol-5-en-22-oate as the main product, and small amounts of (2′R)-3′-cyano-2′-methylpropyl 3β-acetoxy-16β-hydroxy-23,24-bisnorchol-5-en-22-oate and vespertilin acetate.
Keywords
23-Hydroxyiminodiosgenin , Abnormal Beckmann rearrangement , Bisnorcholenes
Journal title
Tetrahedron Letters
Serial Year
2004
Journal title
Tetrahedron Letters
Record number
1842165
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