GB933276A - - Google Patents

Info

Publication number
GB933276A
GB933276A GB2459660A GB2459660A GB933276A GB 933276 A GB933276 A GB 933276A GB 2459660 A GB2459660 A GB 2459660A GB 2459660 A GB2459660 A GB 2459660A GB 933276 A GB933276 A GB 933276A
Authority
GB
United Kingdom
Prior art keywords
pregnan
hydroxy
diketo
lactone
oic acid
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
GB2459660A
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
Publication of GB933276A publication Critical patent/GB933276A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

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

Abstract

The invention comprises the 11,18-lactones of 3,20-diketo-11b -hydroxy-5b -pregnan-18-oic acid and of 3,20-diketo-4#x-bromo-11b -hydroxy-5b -pregnan-18-oic acid, and processes for the preparation of the 11,18-lactone of 3,20-diketo- 11b -hydroxy-pregn-4-en-18-oic acid in which a 3a -acyloxy-18,20b -epoxy-5b -pregnan-11-one is oxidised and saponified to give as intermediate product either 3a -hydroxy-11,20-diketo-5b -pregnan-18-oic acid or the isomeric 20a -hydroxy-18,20-lactone and this latter compound is reduced by reaction with an alkali metal borohydride to form the 11,18-lactone of 3a ,11b ,20b -trihydroxy-5b -pregnan-18-oic acid the hydroxyl groups at the 3 and 20 positions of which are then oxidised to form the 11,18-lactone of 3,20-diketo-11b -hydroxy-5b -pregnan-18-oic acid and finally a 4,5-double bond is introduced by bromination and elimination of the HBr, into the latter to yield the desired 11,18-lactone. The first oxidation may be effected with a mixture of H2SO4 and chromic acid, the reduction with potassium borohydride, the second oxidation with CrO3, in acetic acid, and the dehydrohalogenation with a lithium halide-lithium carbonate couple. Specification 933,277 is referred to.
GB2459660A 1959-08-18 1960-07-14 Expired GB933276A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR802488 1959-08-18

Publications (1)

Publication Number Publication Date
GB933276A true GB933276A (en) 1963-08-08

Family

ID=8718174

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2459660A Expired GB933276A (en) 1959-08-18 1960-07-14

Country Status (2)

Country Link
CH (1) CH395076A (en)
GB (1) GB933276A (en)

Also Published As

Publication number Publication date
CH395076A (en) 1965-07-15

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