Smilagenone → Smilagenone

HRID 2238453Notes

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][CH2:18][C@@H:19]6[CH2:25][C:23](=[O:24])[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.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>>[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[CH2:25][C:23](=[O:24])[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.[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:19]6[C@@:20]([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])[CH2:21][CH2:22][C:23](=[O:24])[CH:25]=6)[CH2:4][CH2:3]1

Participants

Reactant 2

HCID 160498Smilagenone

HCID 2724130Cornforth reagent

Product 2

HCID 160498Smilagenone

HCID 10251134Diosgenone

Procedure

The 3-keto,5β-H steroidal sapogenin starting material may suitably be prepared by oxidation of the corresponding 3-OH sapogenin. For example, sarsasapogenone has been prepared by oxidation with pyridinium dichromate as described by Miles (J. Agric Food Chem., 41, 914-917 (1993)), Jones oxidation as described by Blunden (J. Nat. Prod., 42, 478-482 (1979)) and in WO-98/07741, the disclosures of which are incorporated herein by reference. Smilagenone has been produced from diosgenone (itself prepared by the oxidation of diosgenin) utilizing the reduction of the double bond of the α,β unsaturated ketone [Marker et al., J. Am. Chem. Soc. 2525 (1940), Irismetov & Goryaev, Izv. Akad. Nauk Kaz. SSR, Ser. Khim., 2, 47-52 (1981)].

Sources & evidence

ORD record: ord-ed0283cf07f445b884b048ebc48bdd54
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718792B2

Reaction notes

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