JPS6151591B2 - - Google Patents
Info
- Publication number
- JPS6151591B2 JPS6151591B2 JP9496778A JP9496778A JPS6151591B2 JP S6151591 B2 JPS6151591 B2 JP S6151591B2 JP 9496778 A JP9496778 A JP 9496778A JP 9496778 A JP9496778 A JP 9496778A JP S6151591 B2 JPS6151591 B2 JP S6151591B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- epoxy
- coc
- isopropylidene
- formula
- Prior art date
- 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
Links
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 229930004069 diterpene Natural products 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- -1 diterpene ketone Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000004141 diterpene derivatives Chemical class 0.000 description 3
- 125000000567 diterpene group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- FLJAFHRJXPAASR-LDTXXPTRSA-N (1r,4e,6s,7r,10e,14r)-4-(hydroxymethyl)-10,14-dimethyl-7-prop-1-en-2-yl-15-oxabicyclo[12.1.0]pentadeca-4,10-dien-6-ol Chemical compound C1C\C(CO)=C/[C@H](O)[C@@H](C(=C)C)CC\C(C)=C\CC[C@@]2(C)O[C@@H]21 FLJAFHRJXPAASR-LDTXXPTRSA-N 0.000 description 1
- GCMXDBXZLOLULO-UHFFFAOYSA-N 1,7,11-trimethyl-4-propan-2-ylidene-15-oxabicyclo[12.1.0]pentadeca-6,10-dien-5-one Chemical compound O1C2(CCC(C(C=C(CCC=C(CCC21)C)C)=O)=C(C)C)C GCMXDBXZLOLULO-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- NVFRRJQWRZFDLM-UHFFFAOYSA-N 5-[3-bromo-4-(dimethylamino)phenyl]-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one Chemical compound C1=C(Br)C(N(C)C)=CC=C1C1C(C(=O)CC(C)(C)C2)=C2C2=C3C=CC=CC3=CC=C2N1 NVFRRJQWRZFDLM-UHFFFAOYSA-N 0.000 description 1
- 229930183157 Asperdiol Natural products 0.000 description 1
- FLJAFHRJXPAASR-UHFFFAOYSA-N Asperdiol A Natural products C1CC(CO)=CC(O)C(C(=C)C)CCC(C)=CCCC2(C)OC21 FLJAFHRJXPAASR-UHFFFAOYSA-N 0.000 description 1
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000002768 Kirby-Bauer method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMWZRHGIAVCFNS-UHFFFAOYSA-J aluminum;lithium;tetrahydroxide Chemical compound [Li+].[OH-].[OH-].[OH-].[OH-].[Al+3] VMWZRHGIAVCFNS-UHFFFAOYSA-J 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 231100000263 cytotoxicity test Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9496778A JPS5522625A (en) | 1978-08-03 | 1978-08-03 | Preparation of epoxyditerpene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9496778A JPS5522625A (en) | 1978-08-03 | 1978-08-03 | Preparation of epoxyditerpene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5522625A JPS5522625A (en) | 1980-02-18 |
| JPS6151591B2 true JPS6151591B2 (en, 2012) | 1986-11-10 |
Family
ID=14124680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9496778A Granted JPS5522625A (en) | 1978-08-03 | 1978-08-03 | Preparation of epoxyditerpene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5522625A (en, 2012) |
-
1978
- 1978-08-03 JP JP9496778A patent/JPS5522625A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5522625A (en) | 1980-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0560835B2 (en, 2012) | ||
| JPS5817746B2 (ja) | シクロベンタンユウドウタイノ セイゾウホウホウ | |
| JPS6129360B2 (en, 2012) | ||
| JP2550391B2 (ja) | １β−ヒドロキシビタミンＤ▲下２▼およびＤ▲下３▼の製造方法 | |
| JPS6151591B2 (en, 2012) | ||
| EP0585104B1 (en) | A method of preparing a saturated monocyclic hydrocarbon compound and an intermediate therefor | |
| JPS6151590B2 (en, 2012) | ||
| EP0766660B1 (de) | Cyclohexanon-derivate, verfahren zu deren herstellung und zwischenprodukte des verfahrens | |
| JPS5839156B2 (ja) | 光学活性又はラセミのプロスタグランジンもしくはその薬理的に許容しうる塩の製法 | |
| JPS6212209B2 (en, 2012) | ||
| JPS6151592B2 (en, 2012) | ||
| JPH0684348B2 (ja) | コレカルシフエロール誘導体 | |
| JP3712077B2 (ja) | ヒドロインダン−４−オール誘導体およびその製造方法 | |
| JPH0267250A (ja) | ２，２‐ジフルオロ‐３‐ヒドロキシカルボン酸誘導体の製造法 | |
| JPH05186420A (ja) | １α，２５−ジヒドロキシコレカルシフェロールの製造方法 | |
| JP2975705B2 (ja) | ステロイド誘導体 | |
| CA1338832C (en) | 1.beta., 7, 8-trihydroxy vitamin d_ and 1.beta., 7, 8-trihydroxy vit amin d , or derivatives therefrom and method of preparing the same | |
| JP2001240575A5 (en, 2012) | ||
| JPS62223188A (ja) | ２５−ヒドロキシコレステロ−ル−２６，２３−ラクトン類の製造法 | |
| JPH0220616B2 (en, 2012) | ||
| JPH039892B2 (en, 2012) | ||
| JPS5924139B2 (ja) | エリスロ−２−メチル−１，３−ジオ−ル化合物の製造法 | |
| JPH0825993B2 (ja) | ビタミンｄ２およびｄ３又は活性型ビタミンｄ２およびｄ３の製造方法，並びにその中間体 | |
| JPH03167180A (ja) | ４―置換γ―ラクトン化合物類の製造方法 | |
| JPS6045613B2 (ja) | シス−３−ヘキセン−１，６−ジオ−ルの製造法 |