FR2119855A1 - Synthesis of prostaglandins - without loss of stereospecificity - Google Patents

Synthesis of prostaglandins - without loss of stereospecificity

Info

Publication number
FR2119855A1
FR2119855A1 FR7047004A FR7047004A FR2119855A1 FR 2119855 A1 FR2119855 A1 FR 2119855A1 FR 7047004 A FR7047004 A FR 7047004A FR 7047004 A FR7047004 A FR 7047004A FR 2119855 A1 FR2119855 A1 FR 2119855A1
Authority
FR
France
Prior art keywords
formula
right arrow
stereospecificity
prostaglandins
synthesis
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
FR7047004A
Other languages
French (fr)
Other versions
FR2119855B1 (en
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Priority to FR7047004A priority Critical patent/FR2119855A1/en
Publication of FR2119855A1 publication Critical patent/FR2119855A1/en
Application granted granted Critical
Publication of FR2119855B1 publication Critical patent/FR2119855B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Prepn. of prostaglandin E2 and analogues of formula:- by oxidising cpds (II) of formula:- in an alkaline medium to give mixed epoxides of formula:- which are reduced to cpds. of formula:- which sre hydrolysed in an acid medium to give (I). R' = H, alkyl, n = 2, 3 or 4; m = 3, 4 or 5 indicates 2- or beta-linkage II right arrow III by oxidising with H2O2, t-butyl, peroxide or Nacl III right arrow IV using mixed hydrides, Li in presence of amines or chromous salts. Gp. IV right arrow I using e.g. oxalic acid in aq. media.
FR7047004A 1970-12-29 1970-12-29 Synthesis of prostaglandins - without loss of stereospecificity Granted FR2119855A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7047004A FR2119855A1 (en) 1970-12-29 1970-12-29 Synthesis of prostaglandins - without loss of stereospecificity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7047004A FR2119855A1 (en) 1970-12-29 1970-12-29 Synthesis of prostaglandins - without loss of stereospecificity

Publications (2)

Publication Number Publication Date
FR2119855A1 true FR2119855A1 (en) 1972-08-11
FR2119855B1 FR2119855B1 (en) 1974-04-12

Family

ID=9066480

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7047004A Granted FR2119855A1 (en) 1970-12-29 1970-12-29 Synthesis of prostaglandins - without loss of stereospecificity

Country Status (1)

Country Link
FR (1) FR2119855A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3987085A (en) * 1972-09-15 1976-10-19 The Upjohn Company 8β,11β,12α-PGF2.sub.α compounds
US4084063A (en) * 1972-09-15 1978-04-11 The Upjohn Company 8β,12α-PGF2α Compounds

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL6901591A (en) * 1968-02-01 1969-08-05

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL6901591A (en) * 1968-02-01 1969-08-05

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3987085A (en) * 1972-09-15 1976-10-19 The Upjohn Company 8β,11β,12α-PGF2.sub.α compounds
US4084063A (en) * 1972-09-15 1978-04-11 The Upjohn Company 8β,12α-PGF2α Compounds
US4095036A (en) * 1972-09-15 1978-06-13 The Upjohn Company 8β,12α,15β-PGF2 β Compounds

Also Published As

Publication number Publication date
FR2119855B1 (en) 1974-04-12

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Legal Events

Date Code Title Description
ST Notification of lapse