CA2064481A1 - Method of producing .alpha.,.beta.-unsaturated ketolactones - Google Patents

Method of producing .alpha.,.beta.-unsaturated ketolactones

Info

Publication number
CA2064481A1
CA2064481A1 CA2064481A CA2064481A CA2064481A1 CA 2064481 A1 CA2064481 A1 CA 2064481A1 CA 2064481 A CA2064481 A CA 2064481A CA 2064481 A CA2064481 A CA 2064481A CA 2064481 A1 CA2064481 A1 CA 2064481A1
Authority
CA
Canada
Prior art keywords
beta
alpha
producing
ketolactones
unsaturated
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.)
Granted
Application number
CA2064481A
Other languages
French (fr)
Other versions
CA2064481C (en
Inventor
Ryuji Ueno
Tomio Oda
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.)
R Tech Ueno Ltd
Original Assignee
Ryuji Ueno
Tomio Oda
R-Tech Ueno, Ltd.
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 Ryuji Ueno, Tomio Oda, R-Tech Ueno, Ltd. filed Critical Ryuji Ueno
Publication of CA2064481A1 publication Critical patent/CA2064481A1/en
Application granted granted Critical
Publication of CA2064481C publication Critical patent/CA2064481C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention provides a method of preparing .alpha.,.beta.-unsaturated ketolactones which are useful in the production of prostaglandins having one or more halogen substituent(s) at position 16 or 17 in high yield, in which, a dimethyl (2-oxoalkyl) phosphonate having one or more halogen substituents (as a starting material) is reacted with a bicyclolactone aldehyde in the presence of an alkali metal hydride and a zinc compound.
CA002064481A 1991-04-04 1992-03-31 Method of producing .alpha.,.beta.-unsaturated ketolactones Expired - Fee Related CA2064481C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP71483/1991 1991-04-04
JP7148391 1991-04-04

Publications (2)

Publication Number Publication Date
CA2064481A1 true CA2064481A1 (en) 1992-10-05
CA2064481C CA2064481C (en) 1996-12-24

Family

ID=13461939

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002064481A Expired - Fee Related CA2064481C (en) 1991-04-04 1992-03-31 Method of producing .alpha.,.beta.-unsaturated ketolactones

Country Status (11)

Country Link
US (1) US5229529A (en)
EP (1) EP0507625B1 (en)
JP (1) JPH089608B2 (en)
KR (1) KR970003125B1 (en)
AT (1) ATE141921T1 (en)
CA (1) CA2064481C (en)
DE (1) DE69213067T2 (en)
DK (1) DK0507625T3 (en)
ES (1) ES2093776T3 (en)
GR (1) GR3020903T3 (en)
TW (1) TW197439B (en)

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Also Published As

Publication number Publication date
TW197439B (en) 1993-01-01
GR3020903T3 (en) 1996-11-30
DE69213067T2 (en) 1997-01-16
JPH0592965A (en) 1993-04-16
CA2064481C (en) 1996-12-24
ATE141921T1 (en) 1996-09-15
US5229529A (en) 1993-07-20
KR970003125B1 (en) 1997-03-14
KR920019771A (en) 1992-11-20
EP0507625A1 (en) 1992-10-07
JPH089608B2 (en) 1996-01-31
DK0507625T3 (en) 1996-09-16
ES2093776T3 (en) 1997-01-01
DE69213067D1 (en) 1996-10-02
EP0507625B1 (en) 1996-08-28

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