Constructing 24(23→22)-abeo-Cholestane from Tigogenin in a 20(22→23)-abeo-Way via a PhI(OAc)2‑mediated Favorskii Rearrangement

Constructing 24(23→22)-abeo-Cholestane from Tigogenin in a 20(22→23)-abeo-Way via a PhI(OAc)2‑mediated Favorskii Rearrangement

Transforming tigogenin, a steroidal sapogenin, to a 24(23→22)-abeo-cholestane, which is an unusual structural feature shared by the aglycons of saundersiosides and candicanoside A, is described. The spiroketal of tigogenin was unfolded and the resulting C22-ketone was subjected to Favorskii rearrang...

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Veröffentlicht in:Journal of organic chemistry 2017-04, Vol.82 (8), p.4402-4406
Hauptverfasser: Jiang, Xiao-Ling, Shi, Yong, Tian, Wei-Sheng
Format: Artikel
Sprache:eng
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Zusammenfassung:Transforming tigogenin, a steroidal sapogenin, to a 24(23→22)-abeo-cholestane, which is an unusual structural feature shared by the aglycons of saundersiosides and candicanoside A, is described. The spiroketal of tigogenin was unfolded and the resulting C22-ketone was subjected to Favorskii rearrangement mediated by PhI­(OAc)2/KOH/MeOH to squeeze out the C22 from the side chain, thus reaching the 24(23→22)-abeo-cholestane structure.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b03043