CA1124234A - Anthracycline synthesis - Google Patents

Anthracycline synthesis

Info

Publication number
CA1124234A
CA1124234A CA329,085A CA329085A CA1124234A CA 1124234 A CA1124234 A CA 1124234A CA 329085 A CA329085 A CA 329085A CA 1124234 A CA1124234 A CA 1124234A
Authority
CA
Canada
Prior art keywords
compound
produce
hexahydro
dibenzyloxy
dialkoxy
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
Application number
CA329,085A
Other languages
English (en)
French (fr)
Inventor
Jose Alexander
Lester A. Mitscher
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.)
University of Kansas Endowment Association (KU Endowment)
Original Assignee
University of Kansas Endowment Association (KU Endowment)
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.)
Filing date
Publication date
Application filed by University of Kansas Endowment Association (KU Endowment) filed Critical University of Kansas Endowment Association (KU Endowment)
Priority to CA000397862A priority Critical patent/CA1142177A/en
Application granted granted Critical
Publication of CA1124234A publication Critical patent/CA1124234A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/02—Lithium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/14—Preparation of ethers by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Liquid Crystal Substances (AREA)
  • Saccharide Compounds (AREA)
CA329,085A 1978-06-05 1979-06-05 Anthracycline synthesis Expired CA1124234A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA000397862A CA1142177A (en) 1978-06-05 1982-03-08 Anthracycline synthesis

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US912,842 1978-06-05
US05/912,842 US4244880A (en) 1978-06-05 1978-06-05 Anthracycline synthesis

Publications (1)

Publication Number Publication Date
CA1124234A true CA1124234A (en) 1982-05-25

Family

ID=25432545

Family Applications (1)

Application Number Title Priority Date Filing Date
CA329,085A Expired CA1124234A (en) 1978-06-05 1979-06-05 Anthracycline synthesis

Country Status (6)

Country Link
US (1) US4244880A (Direct)
EP (2) EP0043435A1 (Direct)
JP (1) JPS55390A (Direct)
AT (1) ATE1853T1 (Direct)
CA (1) CA1124234A (Direct)
DE (1) DE2964088D1 (Direct)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4374979A (en) * 1981-04-27 1983-02-22 The University Of Kansas Endowment Association Regiospecific synthesis of anthracyclinone compounds such as daunomycinone
US4515720A (en) * 1983-03-11 1985-05-07 Oregon Graduate Center For Study & Research Method of synthesizing a late-stage intermediate to 11-deoxydaunorubicin and 11-deoxyadriamycin, and two precursors to the object intermediate
US4592867A (en) * 1984-10-19 1986-06-03 Energy Conversion Devices, Inc. Synthesis method for reductant precursor
US5432198A (en) * 1994-08-18 1995-07-11 Sphinx Pharmaceuticals Corporation Vicinal-substituted carbocyclic compounds as therapeutic agents
WO2012001707A1 (en) 2010-07-02 2012-01-05 Indian Council Of Agricultural Research Novel superabsorbents and the method(s) of obtaining the same
CN105151580B (zh) * 2015-08-28 2017-11-24 湖北海洋工程装备研究院有限公司 一种储油罐

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB972082A (en) * 1961-06-07 1964-10-07 Koninklijke Pharma Fab Nv Dihydrodibenzazepinones
CA1017359A (en) * 1972-07-03 1977-09-13 Frederic P. Hauck Substituted cyclic polymethylene phenols
DD122069A1 (Direct) * 1974-04-29 1976-09-12
US4021457A (en) * 1975-11-18 1977-05-03 Research Corporation Intermediates for polycyclic quinonoid antibiotics
US4070382A (en) * 1975-11-18 1978-01-24 Research Corporation Intermediates for polycyclic quinoid antibiotics
US4012448A (en) * 1976-01-15 1977-03-15 Stanford Research Institute Synthesis of adriamycin and 7,9-epiadriamycin
US4116981A (en) * 1977-05-02 1978-09-26 Yuh-Geng Tsay 5,12-epoxy-naphthacene-6,11-dione derivatives

Also Published As

Publication number Publication date
DE2964088D1 (en) 1982-12-30
EP0043435A1 (en) 1982-01-13
ATE1853T1 (de) 1982-12-15
JPS55390A (en) 1980-01-05
US4244880A (en) 1981-01-13
EP0007403A1 (en) 1980-02-06
EP0007403B1 (en) 1982-11-24
JPS6254094B2 (Direct) 1987-11-13

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