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inquiry(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one
castasterone
Conditions | Yield |
---|---|
With trifluoroacetic acid In methanol for 1h; | 98% |
(20S,22R,23R,24S)-23-(1-ethoxyethoxy)-6-ethylenedioxy-2α,3α-isopropylidenedioxy-5α-ergostan-22-ol
castasterone
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran for 3h; Heating; | 94% |
With hydrogenchloride In tetrahydrofuran | 93.5% |
2,3,22,23-tetra-O-acetylcastasterone
castasterone
Conditions | Yield |
---|---|
With potassium hydroxide for 1h; Heating; | 94% |
Δ2-(22R,23R,24S)-22,23-dihydroxy-24-methyl-5α-cholestan-6-one
castasterone
Conditions | Yield |
---|---|
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; water; tert-butyl alcohol for 22h; Ambient temperature; | 93% |
With osmium(VIII) oxide; sulfuric acid; sodium sulfite 1.) pyridine, 15 min, 2.) pyridine, 30 min; Yield given. Multistep reaction; |
(2R,3S,5α,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol
castasterone
Conditions | Yield |
---|---|
With acetic acid at 50℃; for 0.5h; | 82% |
With acetic acid In water at 50 - 60℃; for 1h; | 7.62 g |
With acid Yield given; |
(22E,24S)-5α-ergost-2,22-dien-6-one
castasterone
Conditions | Yield |
---|---|
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; osmium(VIII) oxide; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol for 15h; Ambient temperature; | 80% |
(22E)-24α-methyl-5α-cholesta-2,22-dien-6-one
B
castasterone
Conditions | Yield |
---|---|
With potassium osmate(VI) dihydrate; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); hydroquinidine (anthraquinone-1,4-diyl) diether In water; tert-butyl alcohol at 20℃; for 48h; | A n/a B 63% |
trimethylaluminum
(2R, 3S, 22R, 23S, 24R)-23,24-epoxy-6,6-ethylenedioxy-22-hydroxy-2,3-isopropylidenedioxy-5α-cholestane
castasterone
Conditions | Yield |
---|---|
With n-butyllithium; acetic acid 1) n-hexane, 69 h, room temperature; 2) 50 deg C, 30 min; Yield given. Multistep reaction; |
(2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-2,3-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one
castasterone
Conditions | Yield |
---|---|
With acetic acid In water at 65℃; for 4h; Yield given; |
(22R,23R,24S)-22,23-diacetoxy-2α,3α-isopropylidenedioxy-5α-ergostan-6-one
castasterone
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 3h; Heating; | 458 mg |
(22E,24S)-3α,5-cyclo-5α-ergost-22-en-6-one
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 82 percent / pyridinium tolunen-p-sulfonate, LiBr / N,N-dimethyl-acetamide / 5 h / 160 °C 2: 80 percent / OsO4, K3, 1,4-bis(0-O-dihydroquinidinyl)phthalazine, K2CO3, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 15 h / Ambient temperature View Scheme |
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 57 percent / tetrahydrofuran / 1 h / Ambient temperature 2: 98 percent / propionic acid / xylene / 2 h / Heating 3: LiAlH4 / tetrahydrofuran / 2 h / Heating 4: Et3N / toluene / 2 h / 0 °C 5: LiAlH4 / tetrahydrofuran / Ambient temperature 6: 99 percent / 1 M H2SO4 / acetone / 2 h / Ambient temperature 7: 82 percent / pyridinium tolunen-p-sulfonate, LiBr / N,N-dimethyl-acetamide / 5 h / 160 °C 8: 80 percent / OsO4, K3, 1,4-bis(0-O-dihydroquinidinyl)phthalazine, K2CO3, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 15 h / Ambient temperature View Scheme |
(22S,23Z)-6-(1,3-dioxolan-2-yl)-3α,5-cyclo-26,27-bisnor-5α-cholest-23-en-22-ol
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 98 percent / propionic acid / xylene / 2 h / Heating 2: LiAlH4 / tetrahydrofuran / 2 h / Heating 3: Et3N / toluene / 2 h / 0 °C 4: LiAlH4 / tetrahydrofuran / Ambient temperature 5: 99 percent / 1 M H2SO4 / acetone / 2 h / Ambient temperature 6: 82 percent / pyridinium tolunen-p-sulfonate, LiBr / N,N-dimethyl-acetamide / 5 h / 160 °C 7: 80 percent / OsO4, K3, 1,4-bis(0-O-dihydroquinidinyl)phthalazine, K2CO3, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 15 h / Ambient temperature View Scheme |
(24S)-6-(1,3-dioxolane-2-yl)-24-methyl-3α,5-cyclo-5α-cholest-22-ene
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 99 percent / 1 M H2SO4 / acetone / 2 h / Ambient temperature 2: 82 percent / pyridinium tolunen-p-sulfonate, LiBr / N,N-dimethyl-acetamide / 5 h / 160 °C 3: 80 percent / OsO4, K3, 1,4-bis(0-O-dihydroquinidinyl)phthalazine, K2CO3, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 15 h / Ambient temperature View Scheme |
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: Et3N / toluene / 2 h / 0 °C 2: LiAlH4 / tetrahydrofuran / Ambient temperature 3: 99 percent / 1 M H2SO4 / acetone / 2 h / Ambient temperature 4: 82 percent / pyridinium tolunen-p-sulfonate, LiBr / N,N-dimethyl-acetamide / 5 h / 160 °C 5: 80 percent / OsO4, K3, 1,4-bis(0-O-dihydroquinidinyl)phthalazine, K2CO3, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 15 h / Ambient temperature View Scheme |
(22E,24R)-6-(1,3-dioxolan-2-yl)-24-methyl-3α,5-cyclo-5α-cholest-22-en-26-oic acid ethyl ester
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: LiAlH4 / tetrahydrofuran / 2 h / Heating 2: Et3N / toluene / 2 h / 0 °C 3: LiAlH4 / tetrahydrofuran / Ambient temperature 4: 99 percent / 1 M H2SO4 / acetone / 2 h / Ambient temperature 5: 82 percent / pyridinium tolunen-p-sulfonate, LiBr / N,N-dimethyl-acetamide / 5 h / 160 °C 6: 80 percent / OsO4, K3, 1,4-bis(0-O-dihydroquinidinyl)phthalazine, K2CO3, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 15 h / Ambient temperature View Scheme |
(22E,24R)-6-(1,3-dioxolan-2-yl)-26-methanesulfonyloxy-24-methyl-3α,5-cyclo-5α-cholest-22-ene
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: LiAlH4 / tetrahydrofuran / Ambient temperature 2: 99 percent / 1 M H2SO4 / acetone / 2 h / Ambient temperature 3: 82 percent / pyridinium tolunen-p-sulfonate, LiBr / N,N-dimethyl-acetamide / 5 h / 160 °C 4: 80 percent / OsO4, K3, 1,4-bis(0-O-dihydroquinidinyl)phthalazine, K2CO3, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 15 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: Br2 / methanol 2: acetone / 18 h / Heating 3: NaH / tetrahydrofuran / 0.5 h / 25 °C 4: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 5: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 6: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 7: 96 percent / CSA / 24 h / Ambient temperature 8: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 9: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 10: 98 percent / aq. TFA / methanol / 1 h View Scheme | |
Multi-step reaction with 10 steps 1: Br2 / methanol 2: acetone / 18 h / Heating 3: 1.) NaH, triethylphosphonoacetate, 2.) aq. KOH / 1.) THF, 25 deg C, 30 min, 2.) 25 deg C, 24 h 4: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 5: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 6: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 7: 96 percent / CSA / 24 h / Ambient temperature 8: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 9: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 10: 98 percent / aq. TFA / methanol / 1 h View Scheme |
4-(1-methylethyl)furan-2(5H)-one
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 2: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 3: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 4: 96 percent / CSA / 24 h / Ambient temperature 5: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 6: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 7: 98 percent / aq. TFA / methanol / 1 h View Scheme |
1-(acetyloxy)-3-methyl-2-butanone
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: NaH / tetrahydrofuran / 0.5 h / 25 °C 2: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 3: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 4: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 5: 96 percent / CSA / 24 h / Ambient temperature 6: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 7: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 8: 98 percent / aq. TFA / methanol / 1 h View Scheme | |
Multi-step reaction with 8 steps 1: 1.) NaH, triethylphosphonoacetate, 2.) aq. KOH / 1.) THF, 25 deg C, 30 min, 2.) 25 deg C, 24 h 2: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 3: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 4: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 5: 96 percent / CSA / 24 h / Ambient temperature 6: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 7: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 8: 98 percent / aq. TFA / methanol / 1 h View Scheme |
(22E)-stigmasta-2,22-dien-6-one
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 72 percent / OsO4, NMO, H2O / acetone; 2-methyl-propan-2-ol / 12 h / Ambient temperature 2: 98 percent / CSA / acetonitrile; CH2Cl2 / 1 h / Ambient temperature 3: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C 4: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature 5: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 6: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 7: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 8: 96 percent / CSA / 24 h / Ambient temperature 9: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 10: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 11: 98 percent / aq. TFA / methanol / 1 h View Scheme |
(22E,24S)-3β,5-cyclo-24-ethylcholest-22-en-6-one
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: 80 percent / pyridine hydrochloride, LiBr / N,N-dimethyl-acetamide / 4 h / 160 °C 2: 72 percent / OsO4, NMO, H2O / acetone; 2-methyl-propan-2-ol / 12 h / Ambient temperature 3: 98 percent / CSA / acetonitrile; CH2Cl2 / 1 h / Ambient temperature 4: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C 5: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature 6: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 7: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 8: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 9: 96 percent / CSA / 24 h / Ambient temperature 10: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 11: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 12: 98 percent / aq. TFA / methanol / 1 h View Scheme |
(22E,24S)-2α,3α-dihydroxy-5α-stigmast-22-en-6-one
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 98 percent / CSA / acetonitrile; CH2Cl2 / 1 h / Ambient temperature 2: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C 3: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature 4: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 5: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 6: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 7: 96 percent / CSA / 24 h / Ambient temperature 8: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 9: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 10: 98 percent / aq. TFA / methanol / 1 h View Scheme |
(22E,24S)-2α,3α-Dihydroxy-5α-stigmast-22-en-6-one 2,3-acetonide
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C 2: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature 3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 6: 96 percent / CSA / 24 h / Ambient temperature 7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 9: 98 percent / aq. TFA / methanol / 1 h View Scheme | |
Multi-step reaction with 8 steps 1: 83.0 g / p-TsOH / 3 h / Heating 2: 30 g / ozone, NaHCO3 / methanol; CH2Cl2 / 2 h / -60 - -50 °C 3: n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C 4: 74.6 percent / 1.) triphenylphosphine, benzoic acid, diethyl azodicarboxylate; 2.) K2CO3 / 1.) THF, 5-10 deg C, 30 min; 2.) THF/methanol, reflux, 3 h 5: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h 6: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C 7: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h 8: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C View Scheme | |
Multi-step reaction with 7 steps 1: 83.0 g / p-TsOH / 3 h / Heating 2: 30 g / ozone, NaHCO3 / methanol; CH2Cl2 / 2 h / -60 - -50 °C 3: 26.93 g / n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C 4: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h 5: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C 6: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h 7: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C View Scheme |
(22E,24S)-24-ethyl-3α,5-cyclo-5α-cholest-22-en-6-ol
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1: CrO3, H2SO4 / acetone 2: 80 percent / pyridine hydrochloride, LiBr / N,N-dimethyl-acetamide / 4 h / 160 °C 3: 72 percent / OsO4, NMO, H2O / acetone; 2-methyl-propan-2-ol / 12 h / Ambient temperature 4: 98 percent / CSA / acetonitrile; CH2Cl2 / 1 h / Ambient temperature 5: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C 6: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature 7: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 8: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 9: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 10: 96 percent / CSA / 24 h / Ambient temperature 11: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 12: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 13: 98 percent / aq. TFA / methanol / 1 h View Scheme |
1-bromo-3-methyl-2-butanone
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: acetone / 18 h / Heating 2: NaH / tetrahydrofuran / 0.5 h / 25 °C 3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 6: 96 percent / CSA / 24 h / Ambient temperature 7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 9: 98 percent / aq. TFA / methanol / 1 h View Scheme | |
Multi-step reaction with 9 steps 1: acetone / 18 h / Heating 2: 1.) NaH, triethylphosphonoacetate, 2.) aq. KOH / 1.) THF, 25 deg C, 30 min, 2.) 25 deg C, 24 h 3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 6: 96 percent / CSA / 24 h / Ambient temperature 7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 9: 98 percent / aq. TFA / methanol / 1 h View Scheme |
(20S)-2α,3α-isopropylidenedioxy-5α-pregnan-6-one-20-carbaldehyde
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 2: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 3: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 4: 96 percent / CSA / 24 h / Ambient temperature 5: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 6: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 7: 98 percent / aq. TFA / methanol / 1 h View Scheme |
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 96 percent / CSA / 24 h / Ambient temperature 2: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 3: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 4: 98 percent / aq. TFA / methanol / 1 h View Scheme |
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 2: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 3: 98 percent / aq. TFA / methanol / 1 h View Scheme |
(S)-3-{(4R,5R)-2,2-Dimethyl-5-[(S)-1-((1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-8,8,10a,12a-tetramethyl-5-oxo-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-1-yl)-ethyl]-[1,3]dioxolan-4-yl}-4-methyl-pentanal
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 2: 98 percent / aq. TFA / methanol / 1 h View Scheme |
Conditions | Yield |
---|---|
With pyridine; dmap | 100% |
With dmap In pyridine for 15h; Ambient temperature; | 98% |
With dmap In pyridine at 20℃; for 15h; | 98% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 20℃; Reduction; | A 19% B 77% |
With ethanol; sodium for 2h; Reduction; Heating; | A 53% B 10% |
castasterone
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
Conditions | Yield |
---|---|
Yield given. Multistep reaction; | |
Multi-step reaction with 2 steps 1: pyridine, N,N-dimethylaminopyridine View Scheme |
castasterone
6-deoxo-castasteron
Conditions | Yield |
---|---|
With potassium hydroxide; hydrazine hydrate In diethylene glycol for 2h; Heating; | 1.7 mg |
castasterone
6α-hydroxycastasterone
Conditions | Yield |
---|---|
With ammonia In tetrahydrofuran; methanol at -78℃; for 2h; | 39 mg |
castasterone
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane Ambient temperature; |
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 98 percent / 4-DMAP / pyridine / 15 h / 20 °C 2: BF3*Et2O / hexane; CH2Cl2 / 2.5 h / -20 - -15 °C View Scheme |
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 98 percent / 4-DMAP / pyridine / 15 h / 20 °C 2: BF3*Et2O / hexane; CH2Cl2 / 2.5 h / -20 - -15 °C View Scheme |
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 77 percent / NaBH4 / methanol / 20 °C 2: 80 percent / p-toluenesulfonic acid / CH2Cl2 / 20 °C View Scheme |
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 19 percent / NaBH4 / methanol / 20 °C 2: 68 percent / p-toluenesulfonic acid / CH2Cl2 / 20 °C View Scheme |
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: p-TsOH / CH2Cl2 / Ambient temperature 2: 79 percent / tetrahydrofuran / 2 h 3: 62 percent / aq. AcOH / tetrahydrofuran / 5 h / 70 °C View Scheme |
castasterone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: p-TsOH / CH2Cl2 / Ambient temperature 2: 79 percent / tetrahydrofuran / 2 h View Scheme |
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