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inquiry(+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane for 0.5h; Ambient temperature; | 97% |
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane for 0.5h; | 95% |
With chromium(VI) oxide; sulfuric acid In acetone |
(+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
In water; isopropyl alcohol; acetone |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 98 percent / Ag2CO3, Celite / toluene / Heating 2: (NH4)2Ce(NO3)6, I2 / 2.5 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 98 percent / Ag2CO3, Celite / toluene / Heating 2: 1) (NH4)2Ce(NO3)6, I2, 2) H2 / 2) 5percent Pd/CaCO3 / 1) reflux, 2.5 h, 2) ethyl acetate, 40 psi, overnight View Scheme | |
Multi-step reaction with 4 steps 1: 98 percent / Ag2CO3, Celite / toluene / Heating 3: 85 percent / 1 N aq. KOH / tetrahydrofuran; methanol / 1 h / Ambient temperature 4: 97 percent / N-methylmorpholine N-oxide, tetrapropylammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / Ambient temperature View Scheme |
13β-ethyl-3-hydroxygona-1,3,5(10)-trien-17-one
dimethyl sulfate
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
In acetone Reflux; | 29 g |
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: triethylenediamine / xylene 2: aq. HCl / methanol 3: NaBH4 / methanol 4: H2 / Raney-Ni / dioxane 5: Py 6: KOH / methanol 7: Li, liq. NH3 / diethyl ether; dioxane 8: CrO3, aq. H2SO4 / acetone View Scheme |
(+/-)-13-ethyl-3-methoxygona-1,3,5(10),8,14-pentaen-17-one
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: NaBH4 / methanol 2: H2 / Raney-Ni / dioxane 3: Py 4: KOH / methanol 5: Li, liq. NH3 / diethyl ether; dioxane 6: CrO3, aq. H2SO4 / acetone View Scheme |
2-[2-(3,4-dihydro-6-methoxy-1(2H)-naphthalenylidene)ethyl]-2-ethyl-1,3-cyclopentanedione
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: aq. HCl / methanol 2: NaBH4 / methanol 3: H2 / Raney-Ni / dioxane 4: Py 5: KOH / methanol 6: Li, liq. NH3 / diethyl ether; dioxane 7: CrO3, aq. H2SO4 / acetone View Scheme |
dl-3-Methoxy-13β-ethyl-gona-1,3,5(10),8,14-pentaen-17β-ol
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: H2 / Raney-Ni / dioxane 2: Py 3: KOH / methanol 4: Li, liq. NH3 / diethyl ether; dioxane 5: CrO3, aq. H2SO4 / acetone View Scheme |
13β-ethyl-gon-4-en-3,17-dione
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 2: 85 percent / 1 N aq. KOH / tetrahydrofuran; methanol / 1 h / Ambient temperature 3: 97 percent / N-methylmorpholine N-oxide, tetrapropylammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: lithium bromide; copper(I) bromide / acetonitrile / 17 h / 5 - 25 °C / Inert atmosphere 2: acetone / Reflux View Scheme |
18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Li, liq. NH3, PhNH2 / tetrahydrofuran 2: CrO3, aq. H2SO4 / acetone View Scheme | |
Multi-step reaction with 2 steps 1: Li, liq. NH3 / diethyl ether; dioxane 2: CrO3, aq. H2SO4 / acetone View Scheme |
methanol
13β-ethyl-gon-4-en-3,17-dione
A
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
With copper(ll) bromide for 1h; Heating; | A 12% B 17.56% |
With ammonium cerium(IV) nitrate; hydrogen; iodine; Lindlar's catalyst 1) reflux, 2.5 h, 2) ethyl acetate, 40 psi, overnight; Yield given. Multistep reaction. Yields of byproduct given; |
D-(+)-13β-ethyl-3-methoxygona-1,3,5(10)-trien-17β-yl trifluoroacetate
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / 1 N aq. KOH / tetrahydrofuran; methanol / 1 h / Ambient temperature 2: 97 percent / N-methylmorpholine N-oxide, tetrapropylammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / Ambient temperature View Scheme |
l-3-Methoxy-13β-ethyl-gona-1,3,5(10),8-tetraen-17β-ol-hydrogensuccinat
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: KOH / methanol 2: Li, liq. NH3 / diethyl ether; dioxane 3: CrO3, aq. H2SO4 / acetone View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: Py 2: KOH / methanol 3: Li, liq. NH3 / diethyl ether; dioxane 4: CrO3, aq. H2SO4 / acetone View Scheme |
methanol
13β-ethyl-gon-4-en-3,17-dione
A
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
B
13-Ethyl-3-methoxygona-1,3,5(10),9(11)-tetraen-17-one
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; iodine for 2.5h; Heating; Yields of byproduct given; | A n/a B n/a C 0.38 g |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
toluene-4-sulfonic acid hydrazide
3-Methoxy-18-methyl-17-tosylhydrazono-1,3,5(10)-oestratrien
Conditions | Yield |
---|---|
With sulfuric acid In methanol for 14h; Heating; | 88% |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
acetylene
13β-ethyl-3-methoxy-17α-ethynyl-gona-1,3,5(10)-trien-17β-ol
Conditions | Yield |
---|---|
Stage #1: acetylene With potassium tert-butylate In tetrahydrofuran at 0 - 5℃; for 2h; Stage #2: dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one In tetrahydrofuran at 0 - 5℃; | 78.3% |
With lithium; ethylenediamine In tetrahydrofuran |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
(17S)-13β-Ethyl-3-methoxy-1,3,5(10)-gonatrien-17-spirooxiran
Conditions | Yield |
---|---|
73% |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
With 1-[4-(N,N-dimethylamino)phenyl]ethanol; zirconium(IV) tert-butoxide In toluene at 23℃; for 120h; | 19% |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
Methyltriphenylphosphonium bromide
Conditions | Yield |
---|---|
(i) PhLi, (ii) /BRN= 2059135/; Multistep reaction; |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
1,4-Dichloro-2-butyne
methyl iodide
Conditions | Yield |
---|---|
(i) NaNH2, liq. NH3, (ii) /BRN= 969135/, (iii) /BRN= 2059135/, THF; Multistep reaction; |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
3-Methoxy-18-methyl-1,3,5(10),16-oestratetraen
Conditions | Yield |
---|---|
With methyllithium In diethyl ether for 4h; Ambient temperature; Yield given; |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
phenyllithium
13α-Ethyl-3-methoxy-17-phenyl-1,3,5(10),14(15),16(17)-gonapentaene
Conditions | Yield |
---|---|
With trifluoroacetic acid 1.) THF, benzene, -78 deg C, 15 min; r.t., 30 min, 2.) CH2CL2, r.t., 1 h; Yield given. Multistep reaction; |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
13β-ethyl-3-hydroxygona-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
With pyridine; hydrogenchloride at 180℃; |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
16α,17α-Epoxy-3-methoxy-18-methyl-1,3,5(10)-oestratrien
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
3-Methoxy-18-methyl-1,3,5(10),15-oestratetraen-17α-ol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 87 percent / ethane-1,2-diol / 24 h / 120 °C 4: m-chlorperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 2 h / Ambient temperature 5: 30 percent / o-xylene / 33 h / 140 °C View Scheme | |
Multi-step reaction with 3 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 65 percent / diphenyl diselenide, NaBH4 / ethanol / 18 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 59 percent / lithium bromide / acetic acid / 2 h / Ambient temperature 4: 88 percent / phosphor trichloride oxide / tetrahydrofuran / 18 h / Ambient temperature 5: 1) 1,8-diazobicyclo<5.4.0>undec-7-en; 2) oxalic acid / 1) 30 h at 140 deg C; 2) methanol, water, 24 h at room temp. View Scheme | |
Multi-step reaction with 5 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 79 percent / NaBH4 / ethanol / 80 °C / 1) 20 min.; 2) 17 h 4: 12 percent / NaIO4 / methanol; CH2Cl2 / 48 h / Ambient temperature 5: 50 percent / NaCO3 / o-xylene / 20 h / 140 °C View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
16β-Brom-3-methoxy-18-methyl-1,3,5(10)-oestratrien-17α-ol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 59 percent / lithium bromide / acetic acid / 2 h / Ambient temperature View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
3-Methoxy-18-methyl-1,3,5(10),14,16-oestrapentaen
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 87 percent / ethane-1,2-diol / 24 h / 120 °C 4: m-chlorperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 2 h / Ambient temperature 5: 30 percent / o-xylene / 33 h / 140 °C 6: 55 percent / 70 percent HClO4 / acetone / 0.33 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 65 percent / diphenyl diselenide, NaBH4 / ethanol / 18 h / Heating 4: 55 percent / 70 percent HClO4 / acetone / 0.33 h / Ambient temperature View Scheme | |
Multi-step reaction with 6 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 59 percent / lithium bromide / acetic acid / 2 h / Ambient temperature 4: 88 percent / phosphor trichloride oxide / tetrahydrofuran / 18 h / Ambient temperature 5: 1) 1,8-diazobicyclo<5.4.0>undec-7-en; 2) oxalic acid / 1) 30 h at 140 deg C; 2) methanol, water, 24 h at room temp. 6: 55 percent / 70 percent HClO4 / acetone / 0.33 h / Ambient temperature View Scheme | |
Multi-step reaction with 6 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 79 percent / NaBH4 / ethanol / 80 °C / 1) 20 min.; 2) 17 h 4: 12 percent / NaIO4 / methanol; CH2Cl2 / 48 h / Ambient temperature 5: 50 percent / NaCO3 / o-xylene / 20 h / 140 °C 6: 55 percent / 70 percent HClO4 / acetone / 0.33 h / Ambient temperature View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
3-Methoxy-18-methyl-16β-phenylthio-1,3,5(10)-oestratrien-17α-ol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 79 percent / NaBH4 / ethanol / 80 °C / 1) 20 min.; 2) 17 h View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
3-Methoxy-18-methyl-16β-phenylselenyl-1,3,5(10)-oestratrien-17α-ol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 95 percent / NaBH4 / ethanol / 1) room temp.; 2) reflux at 20 h View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
3-Methoxy-18-methyl-16β-piperidino-1,3,5(10)-oestratien-17α-ol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 87 percent / ethane-1,2-diol / 24 h / 120 °C View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
N-(17α-Hydroxy-3-methoxy-1,3,5(10)-oestratrien-16β-yl)piperidin-N-oxid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 87 percent / ethane-1,2-diol / 24 h / 120 °C 4: m-chlorperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 2 h / Ambient temperature View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
16β-Brom-3-methoxy-18-methyl-17α-(tetrahydro-2-pyranyloxy)-1,3,5(10)-oestratrien
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 59 percent / lithium bromide / acetic acid / 2 h / Ambient temperature 4: 88 percent / phosphor trichloride oxide / tetrahydrofuran / 18 h / Ambient temperature View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
3-Methoxy-18-methyl-16β-phenylsulfonyl-1,3,5(10)-oestratrien-17α-ol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 79 percent / NaBH4 / ethanol / 80 °C / 1) 20 min.; 2) 17 h 4: 4 percent / NaIO4 / methanol; CH2Cl2 / 48 h / Ambient temperature View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
3-Methoxy-18-methyl-16β-phenylselenonyl-1,3,5(10)-oestratrien-17α-ol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 95 percent / NaBH4 / ethanol / 1) room temp.; 2) reflux at 20 h 4: 6 percent / m-chlorperbenzoic acid / CH2Cl2 / 0.25 h / -40 °C View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
(S)-3-Methoxy-18-methyl-16β-phenylsulfinyl-1,3,5(10)-oestratrien-17α-ol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 79 percent / NaBH4 / ethanol / 80 °C / 1) 20 min.; 2) 17 h 4: 34 percent / NaIO4 / methanol; CH2Cl2 / 48 h / Ambient temperature View Scheme |
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
(R)-3-Methoxy-18-methyl-16β-phenylsulfinyl-1,3,5(10)-oestratrien-17α-ol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: methyl lithium / diethyl ether / 4 h / Ambient temperature 2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 79 percent / NaBH4 / ethanol / 80 °C / 1) 20 min.; 2) 17 h 4: 12 percent / NaIO4 / methanol; CH2Cl2 / 48 h / Ambient temperature View Scheme |
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