Diosgenin → Tigogenin

HRID 2238454Notes

Reaction equation

HRID 2238454 reaction equation
[CH3:1][C@H:2]1[CH2:30][O:29][C@@:5]2([O:9][C@H:8]3[CH2:10][C@H:11]4[C@@H:16]5[CH2:17][CH:18]=[C:19]6[CH2:24][C@@H:23]([OH:25])[CH2:22][CH2:21][C@:20]6([CH3:26])[C@H:15]5[CH2:14][CH2:13][C@:12]4([CH3:27])[C@H:7]3[C@@H:6]2[CH3:28])[CH2:4][CH2:3]1>[Pd]>[CH3:1][C@H:2]1[CH2:30][O:29][C@@:5]2([O:9][C@H:8]3[CH2:10][C@H:11]4[C@@H:16]5[CH2:17][CH2:18][C@H:19]6[CH2:24][C@@H:23]([OH:25])[CH2:22][CH2:21][C@:20]6([CH3:26])[C@H:15]5[CH2:14][CH2:13][C@:12]4([CH3:27])[C@H:7]3[C@@H:6]2[CH3:28])[CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 99474Diosgenin

Product 1

HCID 99516Tigogenin

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

This Δ4, 3-keto steroidal sapogenin, for example diosgenone, is itself preferably prepared by an oxidation of the corresponding Δ5, 3-hydroxy steroidal sapogenin, for example diosgenin, to afford the αβ-unsaturated ketone. It will be noted that the direct reduction of diosgenin using palladium on carbon as a catalyst gives predominantly the 5α-product, tigogenin.

Sources & evidence

ORD record
ord-e8cd544d558141a096af67268e0ee44e
Source dataset
uspto-grants-2010_05
Patent number
US07718792B2

Reaction notes

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