Abstract
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.
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