Dehydroepiandrosterone → Dehydroepiandrosterone

HRID 1003233

Reaction equation

HRID 1003233 reaction equation
O1C(O)C[C@@H](C(C)C)C[CH:2]1[C@H]([C@@H]1[C@]2(C)[C@@H]([C@H]3[C@H](CC2)[C@]2(C)C(CC(O)CC2)CC3)C(=O)C1)C.[CH3:34][C@@:35]12[C:43](=[O:44])[CH2:42][CH2:41][C@H:40]1[C@@H:39]1[CH2:45][CH:46]=[C:47]3[CH2:52][C@@H:51]([OH:53])[CH2:50][CH2:49][C@:48]3([CH3:54])[C@H:38]1[CH2:37][CH2:36]2>>[C:2].[C:34].[CH3:34][C@@:35]12[C:43](=[O:44])[CH2:42][CH2:41][C@H:40]1[C@@H:39]1[CH2:45][CH:46]=[C:47]3[CH2:52][C@@H:51]([OH:53])[CH2:50][CH2:49][C@:48]3([CH3:54])[C@H:38]1[CH2:37][CH2:36]2

Participants

4

Reactant 2

HCID 5881DehydroepiandrosteroneHCID 6962581522,29-EPOXY-3,29-DIHYDROXY-14beta-STIGMASTAN-15-ONE

Product 2

HCID 5881DehydroepiandrosteroneHCID 178420941HCID 178420941, compound

Procedure

The synthesis of 22,29-epoxy-3,29-dihydroxy-14,-stigmastan-15-one (260) can be accomplished in ten steps from dehydroisoandrosterone (247). Catalytic hydrogenation of the Δ5 carbon-carbon double bond in compound 247 yields compound 250, which contains a trans-fused A/B ring-system. Compound 247 is dissolved in EtOAc and 10% Pd/C is added. The mixture is stirred under H2 at room temperature overnight. Filtration through celite and concentration yields compound 250, which can be used directly in the next reaction.

Workup

  1. customThe synthesis of 22,29-epoxy-3,29-dihydroxy-14

Sources & evidence

ORD record
ord-8f631006734d4e3a8529b1bee669ef6f
Source dataset
uspto-grants-2000_04
Patent number
US06046185

Linked notes

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