CA1055015A - Procede de preparation d'un derive de steroides - Google Patents

Procede de preparation d'un derive de steroides

Info

Publication number: CA1055015A
Authority: CA; Canada
Prior art keywords: cholesta; trien; carried out; ether; boron hydride
Prior art date: 1973-12-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA290,600A

Other languages

English (en)

Inventor

Masayuki Ishikawa

Chikara Kaneko

Tatsuo Suda

Akiko Sugimoto

Satoshi Sasaki

Yukuo Eguchi

Sachiko Yamada

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wisconsin Alumni Research Foundation

Original Assignee

Wisconsin Alumni Research Foundation

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-12-03

Filing date

1977-11-10

Publication date

1979-05-22

1973-12-03 Priority claimed from JP13439473A external-priority patent/JPS537426B2/ja

1973-12-03 Priority claimed from JP13439573A external-priority patent/JPS5314064B2/ja

1974-12-02 Priority claimed from CA215,048A external-priority patent/CA1034114A/fr

1977-11-10 Application filed by Wisconsin Alumni Research Foundation filed Critical Wisconsin Alumni Research Foundation

1979-05-22 Application granted granted Critical

1979-05-22 Publication of CA1055015A publication Critical patent/CA1055015A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 41
238000002360 preparation method Methods 0.000 title claims abstract description 11
150000003431 steroids Chemical class 0.000 title 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims abstract description 12
229910010277 boron hydride Inorganic materials 0.000 claims abstract description 12
229910052751 metal Inorganic materials 0.000 claims abstract description 11
239000002184 metal Substances 0.000 claims abstract description 11
239000003054 catalyst Substances 0.000 claims abstract description 7
NIJCHQWGAFQPFT-GYKMGIIDSA-N (8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-8,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 NIJCHQWGAFQPFT-GYKMGIIDSA-N 0.000 claims abstract description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
239000002904 solvent Substances 0.000 claims description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 13
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
-1 alkali metal alkoxide Chemical class 0.000 claims description 9
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical group [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 7
239000001110 calcium chloride Substances 0.000 claims description 7
229910001628 calcium chloride Inorganic materials 0.000 claims description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
239000012298 atmosphere Substances 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 5
229910052786 argon Inorganic materials 0.000 claims description 5
229960001760 dimethyl sulfoxide Drugs 0.000 claims description 5
ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical group [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 claims description 5
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
XLKNMWIXNFVJRR-UHFFFAOYSA-N boron potassium Chemical compound [B].[K] XLKNMWIXNFVJRR-UHFFFAOYSA-N 0.000 claims description 4
239000011261 inert gas Substances 0.000 claims description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 3
229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
PPTSBERGOGHCHC-UHFFFAOYSA-N boron lithium Chemical compound [Li].[B] PPTSBERGOGHCHC-UHFFFAOYSA-N 0.000 claims description 2
229910001622 calcium bromide Inorganic materials 0.000 claims description 2
WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 claims description 2
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims description 2
229910001623 magnesium bromide Inorganic materials 0.000 claims description 2
229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
229910052708 sodium Inorganic materials 0.000 claims 3
239000011734 sodium Substances 0.000 claims 3
239000012300 argon atmosphere Substances 0.000 claims 1
230000005855 radiation Effects 0.000 abstract description 6
150000002978 peroxides Chemical class 0.000 abstract description 5
239000007858 starting material Substances 0.000 abstract description 5
239000003795 chemical substances by application Substances 0.000 abstract description 4
229960002061 ergocalciferol Drugs 0.000 abstract description 3
239000011653 vitamin D2 Substances 0.000 abstract description 3
MECHNRXZTMCUDQ-UHFFFAOYSA-N Vitamin D2 Natural products C1CCC2(C)C(C(C)C=CC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C MECHNRXZTMCUDQ-UHFFFAOYSA-N 0.000 abstract description 2
QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 abstract description 2
230000001749 antrachitic effect Effects 0.000 abstract description 2
230000004071 biological effect Effects 0.000 abstract description 2
235000001892 vitamin D2 Nutrition 0.000 abstract description 2
MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 abstract description 2
239000011647 vitamin D3 Substances 0.000 abstract description 2
235000005282 vitamin D3 Nutrition 0.000 abstract description 2
QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 abstract description 2
229940021056 vitamin d3 Drugs 0.000 abstract description 2
OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 abstract 2
150000002118 epoxides Chemical class 0.000 abstract 1
230000001590 oxidative effect Effects 0.000 abstract 1
239000011782 vitamin Substances 0.000 abstract 1
229940088594 vitamin Drugs 0.000 abstract 1
229930003231 vitamin Natural products 0.000 abstract 1
235000013343 vitamin Nutrition 0.000 abstract 1
150000003722 vitamin derivatives Chemical class 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 18
239000000243 solution Substances 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000007788 liquid Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
ISULLEUFOQSBGY-UHFFFAOYSA-N 4-phenyl-1,2,4-triazole-3,5-dione Chemical compound O=C1N=NC(=O)N1C1=CC=CC=C1 ISULLEUFOQSBGY-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
101150041968 CDC13 gene Proteins 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
238000013019 agitation Methods 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 5
238000001819 mass spectrum Methods 0.000 description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000007789 gas Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000002211 ultraviolet spectrum Methods 0.000 description 4
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 3
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000007269 dehydrobromination reaction Methods 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000006239 protecting group Chemical class 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
WRFWAYDBNCOWRA-UHFFFAOYSA-N 3,4-dichloro-1-(6-iodo-4-oxo-2-thiophen-2-ylquinazolin-3-yl)pyrrole-2,5-dione Chemical compound O=C1C(Cl)=C(Cl)C(=O)N1N1C(=O)C2=CC(I)=CC=C2N=C1C1=CC=CS1 WRFWAYDBNCOWRA-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
ZQMWFABJLXYBSW-UHFFFAOYSA-N 4-(4-methylphenyl)-1,2,4-triazole-3,5-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)N=NC1=O ZQMWFABJLXYBSW-UHFFFAOYSA-N 0.000 description 1
XRYKNRLGZZNWEE-UHFFFAOYSA-N 4-methyl-1,2,4-triazole-3,5-dione Chemical compound CN1C(=O)N=NC1=O XRYKNRLGZZNWEE-UHFFFAOYSA-N 0.000 description 1
CROZQXPNRTXPGL-UHFFFAOYSA-N 4-phenyl-3,5-dihydro-1,2,4-triazole Chemical compound C1N=NCN1c1ccccc1 CROZQXPNRTXPGL-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000007670 refining Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Steroid Compounds (AREA)

CA290,600A 1973-12-03 1977-11-10 Procede de preparation d'un derive de steroides Expired CA1055015A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP13439473A JPS537426B2 (fr)	1973-12-03	1973-12-03
JP13439573A JPS5314064B2 (fr)	1973-12-03	1973-12-03
CA215,048A CA1034114A (fr)	1973-12-03	1974-12-02	Modes de preparation de derives steroides

Publications (1)

Publication Number	Publication Date
CA1055015A true CA1055015A (fr)	1979-05-22

Family

ID=27163738

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA290,600A Expired CA1055015A (fr)	1973-12-03	1977-11-10	Procede de preparation d'un derive de steroides

Country Status (1)

Country	Link
CA (1)	CA1055015A (fr)

1977
- 1977-11-10 CA CA290,600A patent/CA1055015A/fr not_active Expired

Publication	Publication Date	Title
DE2535308C2 (de)	1983-08-04	1&alpha;, 2&alpha;-Dihydroxycholecalciferol, Verfahren zu seiner Herstellung und seine Verwendung
DE3005736A1 (de)	1980-08-21	Vitamin d tief 3 -derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneistoffe
Beckwith et al.	1976	Specific β-scission of 3β, 5-cyclocholestan-6-yl radical
US3929770A (en)	1975-12-30	Process for preparation of steroid derivative
US4022768A (en)	1977-05-10	Process for preparation of 1α,25-dihydroxycholecalciferol
JP5430603B2 (ja)	2014-03-05	ググルステロン及びググルステロールの製造方法
Kocovský et al.	1999	An Approach toward the Triquinane-Type Skeleton via Reagent-Controlled Skeletal Rearrangements. A Facile Method for Protection− Deprotection of Organomercurials, Tuning the Selectivity of Wagner− Meerwein Migrations, and a New Route to Annulated Lactones
CA1055015A (fr)	1979-05-22	Procede de preparation d'un derive de steroides
Luteijn et al.	1981	Stereospecific synthesis of 9. alpha.-(acetoxymethyl)-8. alpha., 8'-epoxy-3. alpha., 4, 4-trimethyl-trans-decalin-1. alpha.-ol acetate, a model for the investigation of structure-activity relationships of the insect antifeedant neoclerodanes
CA1327977C (fr)	1994-03-22	Methode pour la preparation de composes 1.alpha.-hydroxyvitamine d et 1.alpha.-hydroxyprevitamine d, et compose d'addition de la previtamine d ou du tachysterol avec un dienophileapproprie
Matsumoto et al.	1987	The synthesis of ar-abietatrien-12, 16-oxide and its C-15 epimer.
JPH0324053A (ja)	1991-02-01	付加物―アルデヒドおよびビタミン―ｄ化合物の調製のためのその使用
Paryzek et al.	1997	Ozonolysis of cholesterol and other Δ 5-steroids in the presence of alcohols: a revised mechanism and hydroperoxide structure of the solvent-participated product, confirmed by X-ray analysis
Matsumoto et al.	1982	Total synthesis of (.+-.)-pisiferic acid, methyl (.+-.)-pisiferate, and (.+-.)-pisiferol.
US4298537A (en)	1981-11-03	Process for producing steroid compounds having an oxo group in the side chain
HU176008B (en)	1980-11-28	Process for preparing tropane derivatives
Li et al.	1983	Synthesis of (23R)-and (23S)-methylcholesterol
JP2953665B2 (ja)	1999-09-27	ステロイド誘導体の製造方法
DeNinno et al.	1997	The 14C radiolabelled synthesis of the cholesterol absorption inhibitor CP-148,623. A novel method for the incorporation of a 14C label in enones
JPS6258351B2 (fr)	1987-12-05
Barton et al.	1966	Photochemical transformations—XX: A partial synthesis of cincholic acid
Cambie et al.	1982	The Woodward-Prévost reaction with 5α-Androst-7-ene
Shamsuzzaman et al.	1991	A convenient method for the synthesis of 3. beta.-hydroxy 4-en-6-one steroids
Bjelaković et al.	2002	Hydride reduction of B-norcholestane 5α, 6α-epoxide
ITMI941846A1 (it)	1996-03-09	Processo per la preparazione del gestodene