Dehydroepiandrosterone → Dehydroepiandrosterone

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

Reactant 2

HCID 5881Dehydroepiandrosterone

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

Product 2

HCID 5881Dehydroepiandrosterone

HCID 178420941HCID 178420941, compound

Procedure

The synthesis of 22,29-epoxy-3,29-dihydroxy-14β-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.