Synthesis of “glycospirostanes”—Steroid sapogenins with a sugar-like ring F

The synthesis of two “glycospirostanes” from 23-oxotigogenin acetate is described. (23 S,24 S,25 R)-5α-Spirostane-3β,23,24,25-tetraol was obtained by dehydrogenation followed by stereoselective reduction of the 23-oxo group and OsO 4 dihydroxylation of the C24–C25 double bond. Allylic hydroxylation...

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Veröffentlicht in:	Steroids 2008-04, Vol.73 (4), p.449-457
Hauptverfasser:	López, Yliana, Jastrzębska, Izabella, Santillan, Rosa, Morzycki, Jacek W.
Format:	Artikel
Sprache:	eng
Schlagworte:	Biological and medical sciences Crystallography, X-Ray Cytotoxicity Dihydroxylation Fundamental and applied biological sciences. Psychology Glycospirostanes Models, Chemical Molecular Structure Sapogenins - chemical synthesis Sapogenins - chemistry Saponins Spirostans - chemical synthesis Spirostans - chemistry Stereoisomerism Vertebrates: endocrinology
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Zusammenfassung:	The synthesis of two “glycospirostanes” from 23-oxotigogenin acetate is described. (23 S,24 S,25 R)-5α-Spirostane-3β,23,24,25-tetraol was obtained by dehydrogenation followed by stereoselective reduction of the 23-oxo group and OsO 4 dihydroxylation of the C24–C25 double bond. Allylic hydroxylation with SeO 2 of 3β-acetoxy-5α-spirost-23-ene obtained from 23-oxotigogenin acetate followed by OsO 4 dihydroxylation of the C23–C24 double bond afforded (23 R,24 S,25 R)-5α-spirostane-3β,23,24,25-tetraol.
ISSN:	0039-128X 1878-5867
DOI:	10.1016/j.steroids.2007.12.015