CA1097345A - Intermediaires pour la production de quinonoides polycycliques antibiotiques - Google Patents

Intermediaires pour la production de quinonoides polycycliques antibiotiques

Info

Publication number: CA1097345A
Authority: CA; Canada
Prior art keywords: mixture; acid; reaction; compound; suitably
Prior art date: 1975-11-18
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

CA300,133A

Other languages

English (en)

Inventor

Andrew S. Kende

John E. Mills

Yuh-Geng Tsay

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.)

Research Corp

Original Assignee

Research Corp

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.)

1975-11-18

Filing date

1978-03-31

Publication date

1981-03-10

1975-11-18 Priority claimed from US05/632,939 external-priority patent/US4070382A/en

1978-03-31 Application filed by Research Corp filed Critical Research Corp

1978-03-31 Priority to CA300,133A priority Critical patent/CA1097345A/fr

1981-03-10 Application granted granted Critical

1981-03-10 Publication of CA1097345A publication Critical patent/CA1097345A/fr

Status Expired legal-status Critical Current

Links

239000000543 intermediate Substances 0.000 title abstract description 6
239000003242 anti bacterial agent Substances 0.000 title abstract description 3
229940088710 antibiotic agent Drugs 0.000 title abstract 2
125000003367 polycyclic group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 60
239000000203 mixture Substances 0.000 claims description 76
238000000034 method Methods 0.000 claims description 51
239000002253 acid Substances 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
KKWYCOVNHPJLPP-UHFFFAOYSA-N 5,7,12-trihydroxy-3h-tetracene-2,6,11-trione Chemical compound O=C1CC=C2C(O)=C(C(=O)C=3C(O)=CC=CC=3C3=O)C3=C(O)C2=C1 KKWYCOVNHPJLPP-UHFFFAOYSA-N 0.000 abstract description 13
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 abstract description 10
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 abstract description 8
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 abstract description 7
230000015572 biosynthetic process Effects 0.000 abstract description 7
238000003786 synthesis reaction Methods 0.000 abstract description 7
WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 abstract description 6
229940009456 adriamycin Drugs 0.000 abstract description 5
238000002360 preparation method Methods 0.000 abstract description 4
230000000259 anti-tumor effect Effects 0.000 abstract description 2
229960000975 daunorubicin Drugs 0.000 abstract description 2
150000004053 quinones Chemical class 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 58
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238000006243 chemical reaction Methods 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 41
230000000875 corresponding effect Effects 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
239000000243 solution Substances 0.000 description 36
239000002904 solvent Substances 0.000 description 36
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
229960001701 chloroform Drugs 0.000 description 29
YOFDHOWPGULAQF-MQJDWESPSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound C1[C@@](O)(C(C)=O)C[C@H](O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-MQJDWESPSA-N 0.000 description 28
YOFDHOWPGULAQF-UHFFFAOYSA-N Daunomycin-Aglycone Natural products C1C(O)(C(C)=O)CC(O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
-1 polycyclic quinones Chemical class 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 15
229960005419 nitrogen Drugs 0.000 description 15
239000003960 organic solvent Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
229940022663 acetate Drugs 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
238000007792 addition Methods 0.000 description 13
229940052303 ethers for general anesthesia Drugs 0.000 description 13
239000007858 starting material Substances 0.000 description 13
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 11
150000002148 esters Chemical class 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
239000000284 extract Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
239000007787 solid Substances 0.000 description 9
OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 8
ZVOJSVUMROYCFJ-UHFFFAOYSA-N 5,7,12-trihydroxy-3,4-dihydro-1h-tetracene-2,6,11-trione Chemical compound C1C(=O)CCC2=C1C(O)=C1C(=O)C(C=CC=C3O)=C3C(=O)C1=C2O ZVOJSVUMROYCFJ-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
229910052500 inorganic mineral Inorganic materials 0.000 description 8
239000011707 mineral Substances 0.000 description 8
235000010755 mineral Nutrition 0.000 description 8
239000007800 oxidant agent Substances 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 7
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 7
238000001914 filtration Methods 0.000 description 7
235000011167 hydrochloric acid Nutrition 0.000 description 7
229960000443 hydrochloric acid Drugs 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
229960004337 hydroquinone Drugs 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
XYDJGVROLWFENK-YBTHPKLGSA-N (7s,9s)-9-acetyl-4,6,7,9,11-pentahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C(O)=C1[C@@H](O)C[C@@](C(=O)C)(O)CC1=C2O XYDJGVROLWFENK-YBTHPKLGSA-N 0.000 description 5
239000007818 Grignard reagent Substances 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
238000010828 elution Methods 0.000 description 5
125000001033 ether group Chemical group 0.000 description 5
150000008282 halocarbons Chemical class 0.000 description 5
239000000463 material Substances 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
230000001590 oxidative effect Effects 0.000 description 5
239000003495 polar organic solvent Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
238000003756 stirring Methods 0.000 description 5
GEFIEMUYJSWDLW-UHFFFAOYSA-N 1,4,5-trimethoxyanthracene-9,10-dione Chemical compound O=C1C2=C(OC)C=CC(OC)=C2C(=O)C2=C1C=CC=C2OC GEFIEMUYJSWDLW-UHFFFAOYSA-N 0.000 description 4
IQWXJYDTZDSHFZ-UHFFFAOYSA-N 1,8-dihydroxytetracene-5,6,11,12-tetrone Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C(=O)C1=CC=C(O)C=C1C2=O IQWXJYDTZDSHFZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
238000005698 Diels-Alder reaction Methods 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
KNCZUXHSQJQWIB-UHFFFAOYSA-N anthracene-1,4,9,10-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(=O)C=CC2=O KNCZUXHSQJQWIB-UHFFFAOYSA-N 0.000 description 4
230000031709 bromination Effects 0.000 description 4
238000005893 bromination reaction Methods 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
230000017858 demethylation Effects 0.000 description 4
238000010520 demethylation reaction Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
235000006408 oxalic acid Nutrition 0.000 description 4
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150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
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238000013019 agitation Methods 0.000 description 3
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125000001743 benzylic group Chemical group 0.000 description 3
DYBUYNXFWDRGMW-UHFFFAOYSA-N buta-1,3-dien-2-ol Chemical compound OC(=C)C=C DYBUYNXFWDRGMW-UHFFFAOYSA-N 0.000 description 3
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JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000006345 epimerization reaction Methods 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
150000004795 grignard reagents Chemical class 0.000 description 3
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239000011261 inert gas Substances 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
229940101209 mercuric oxide Drugs 0.000 description 3
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 3
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238000010992 reflux Methods 0.000 description 3
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FTZHOLZFVCGEJD-UHFFFAOYSA-N (5,8-dimethoxy-9,10-dioxoanthracen-1-yl) acetate Chemical compound O=C1C2=C(OC(C)=O)C=CC=C2C(=O)C2=C1C(OC)=CC=C2OC FTZHOLZFVCGEJD-UHFFFAOYSA-N 0.000 description 2
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PRKNCOCERFKSLP-UHFFFAOYSA-N 1,4,5-trihydroxyanthraquinone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C=CC=C2O PRKNCOCERFKSLP-UHFFFAOYSA-N 0.000 description 2
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IDPSDGQOPKQJFM-UHFFFAOYSA-N 1,6,8,11-tetrahydroxytetracene-5,12-dione Chemical compound C1=CC=C2C(=O)C3=C(O)C4=CC(O)=CC=C4C(O)=C3C(=O)C2=C1O IDPSDGQOPKQJFM-UHFFFAOYSA-N 0.000 description 2
CQGDBBBZCJYDRY-UHFFFAOYSA-N 1-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2OC CQGDBBBZCJYDRY-UHFFFAOYSA-N 0.000 description 2
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
FIAOQESWAROILA-UHFFFAOYSA-N 2-(2,5-dimethoxybenzoyl)-6-methoxybenzoic acid Chemical compound COC1=CC=C(OC)C(C(=O)C=2C(=C(OC)C=CC=2)C(O)=O)=C1 FIAOQESWAROILA-UHFFFAOYSA-N 0.000 description 2
VNMCKLVHDJADEB-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-ylcyclohexyl)oxyacetyl chloride Chemical compound CC(C)C1CCC(C)CC1OCC(Cl)=O VNMCKLVHDJADEB-UHFFFAOYSA-N 0.000 description 2
KRKJKLCCCGDNCY-UHFFFAOYSA-N 4-methoxy-2-benzofuran-1,3-dione Chemical compound COC1=CC=CC2=C1C(=O)OC2=O KRKJKLCCCGDNCY-UHFFFAOYSA-N 0.000 description 2
AEFOCMBMSVLYIF-UHFFFAOYSA-N 5-hydroxyanthracene-1,4,9,10-tetrone Chemical compound OC1=CC=CC(C2=O)=C1C(=O)C1=C2C(=O)C=CC1=O AEFOCMBMSVLYIF-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
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239000004215 Carbon black (E152) Substances 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
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150000001242 acetic acid derivatives Chemical class 0.000 description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
229940040526 anhydrous sodium acetate Drugs 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
239000012267 brine Substances 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
XREUEWVEMYWFFA-CSKJXFQVSA-N carminomycin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XREUEWVEMYWFFA-CSKJXFQVSA-N 0.000 description 2
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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA300,133A 1975-11-18 1978-03-31 Intermediaires pour la production de quinonoides polycycliques antibiotiques Expired CA1097345A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA300,133A CA1097345A (fr)	1975-11-18	1978-03-31	Intermediaires pour la production de quinonoides polycycliques antibiotiques

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US632,939		1975-11-18
US05/632,939 US4070382A (en)	1975-11-18	1975-11-18	Intermediates for polycyclic quinoid antibiotics
CA265,482A CA1097342A (fr)	1975-11-18	1976-11-12	Intermediaires de quinonoides polycycliques antibiotiques
CA300,133A CA1097345A (fr)	1975-11-18	1978-03-31	Intermediaires pour la production de quinonoides polycycliques antibiotiques

Publications (1)

Publication Number	Publication Date
CA1097345A true CA1097345A (fr)	1981-03-10

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Application Number	Title	Priority Date	Filing Date
CA300,133A Expired CA1097345A (fr)	1975-11-18	1978-03-31	Intermediaires pour la production de quinonoides polycycliques antibiotiques

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1978
- 1978-03-31 CA CA300,133A patent/CA1097345A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-03-10	MKEX	Expiry

Publication	Publication Date	Title
CA1097342A (fr)	1981-03-10	Intermediaires de quinonoides polycycliques antibiotiques
Tashiro et al.	1982	Metacyclophanes and related compounds. 7. Preparation and reduction of [2.2] metacyclophanequinone
Naya et al.	1990	Sesquiterpenes from the rhizomes of Ligularia dentata Hara.
US4127608A (en)	1978-11-28	Synthesis of Vitamin E
de Koning et al.	2001	The synthesis of isochroman-4-ols and isochroman-3-ols: models for naturally occurring benzo [g] isochromanols
US4154745A (en)	1979-05-15	Isobenzofuran route to anthracycloquinones
Hauser et al.	1988	Regio-and stereospecific syntheses of 4-deoxyadriamycinone and 4, 6-dideoxyadriamycinone from a common intermediate
Brimble et al.	2001	C-Glycosylation of tri-O-benzyl-2-deoxy-D-glucose: synthesis of naphthyl-substituted 3, 6-dioxabicyclo [3.2. 2] nonanes
US4310465A (en)	1982-01-12	Synthesis of vitamin E and quinone intermediates
US4021457A (en)	1977-05-03	Intermediates for polycyclic quinonoid antibiotics
Iwao et al.	1987	Utilization of sulfide, sulfoxide, and sulfone groups as regiochemical control elements in the Diels-Alder reaction of naphthoquinones.
CA1097345A (fr)	1981-03-10	Intermediaires pour la production de quinonoides polycycliques antibiotiques
Sundararaman et al.	1977	Cationic cyclizations of labda-8 (17), 12-and labda-8 (17), 13 (16)-dien-14-ol
Sviridov et al.	1991	Stereocontrolled synthesis of erythronolides A and B in A (C5-C9)+(C3-C4)+(C1-C2)+(C11-C13) sequence from 1, 6-anhydro-β-D-glucopyranose (levoglucosan). Part 2.
US4185154A (en)	1980-01-22	Synthesis of vitamin E
Muschik et al.	1979	Synthesis of the 1-, 2-, 3-, and 4-hydroxy isomers of benz [a] anthracene-7, 12-dione, benz [a] anthracene, and 7, 12-dimethylbenz [a] anthracene
US4298535A (en)	1981-11-03	Anthracyclinones
US4243598A (en)	1981-01-06	Synthesis of vitamin E
Joshi et al.	1977	Isolation and identification of two phenolic ketones and a chromone from Dysophylla stellata Benth.
Niwa et al.	1976	Chemical correlations of α-santonin with (+)-junenol and acolamone
CA1097343A (fr)	1981-03-10	Intermediaries de quinonoides polycycliques antibiotiques
Marcos et al.	1994	Synthesis of a 1-acetyl-3α, 6-dimethyl-hexahydroazulene. Versatile intermediate for the preparation of terpenoids with bicycle [5.3. O] decane system
Lagnel et al.	2000	Synthesis of drimanes from (+)-larixol
Sicherer‐Roetman et al.	1985	Investigations into the total synthesis of momilactones. Stereoselective preparation of (±)‐4, 4‐dinor‐9βH‐pimara‐7, 19‐diene
CA1097344A (fr)	1981-03-10	Intermediaries pour la production de quinonoides polycycliques antibiotiques