GB813317A - New steroid compounds and method for the transformation of epoxy-ketones by the action of fermenting yeast - Google Patents

New steroid compounds and method for the transformation of epoxy-ketones by the action of fermenting yeast

Info

Publication number
GB813317A
GB813317A GB2456/56A GB245656A GB813317A GB 813317 A GB813317 A GB 813317A GB 2456/56 A GB2456/56 A GB 2456/56A GB 245656 A GB245656 A GB 245656A GB 813317 A GB813317 A GB 813317A
Authority
GB
United Kingdom
Prior art keywords
methyl
epoxy
pregnadiene
diol
triol
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
GB2456/56A
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.)
Pfizer Italia SRL
Original Assignee
Farmaceutici Italia SpA
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 Farmaceutici Italia SpA filed Critical Farmaceutici Italia SpA
Publication of GB813317A publication Critical patent/GB813317A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P33/00—Preparation of steroids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention comprises pregnan-3,4,5-triol-20 - one, 17b - methyl - 18 - nor - D 4,13 - 17a -pregnadiene-16a , 20-diol-3-one, its diacetate, 17b - methyl - 18 - nor - D 5,13 - 17a - pregnadiene - 3b ,16a ,20 - triol, its triacetate, 17b -methyl - 18 - nor - D 13 - 17a - pregnene - 16a , 20-diol-3-one and 17b -methyl-18-nor- D 5,13-17a -pregnadiene - 3b ,16a ,20,21 - tetrol 21 - acetate, together with processes for converting an a ,b -epoxyketone to a polyhydric compound having hydroxyl groups attached to the a - and b -carbon atoms and in which the carbonyl group is reduced to a secondary hydroxyl group, and for converting an a -b -epoxy-ketone of partial formula: <FORM:0813317/IV (b)/1> (where R is alkyl containing not more than four carbon atoms or an acylated hydroxyalkyl group) especially a 16 : 17 - oxido - 20 - keto steroid, into the corresponding molecularly rearranged unsaturated diol of partial formula: <FORM:0813317/IV (b)/2> by the action of fermenting yeast in each case. In examples: (1) benzalacetophenone epoxide in ethanol is added to fermenting yeast and the mixture left for 10 days at 32 DEG C., adding more yeast at 48 hour intervals; 1,3-diphenylglycerol is then isolated by extraction with ethyl acetate; (2) 4,5-epoxy-pregnan-3,20-dione is treated with yeast as in (1), giving pregnane-3,4,5-triol-20-one; similarly (3) 16,17- epoxy - progesterone gives 17b - methyl - 18 - nor - D 4,13 - 17a - pregnadiene - 16a ,20 - diol-3-one, characterized as its diacetate; (4) 16,17-epoxy - D 5 - pregnen - 3b - ol - 20 - one yields 17b - methyl - 18 - nor - D 5,13 - 17a - pregnadiene-3b ,16a ,20-triol and then the triacetate; (5) 16,17 - epoxy - pregnane - 3,20 - dione gives 17b - methyl - 18 - nor - D 13 - 17a - pregnene-16a ,20 - diol - 3 - one; and (6) 16,17 - epoxy-D 5 - pregnene - 3b ,21 - diol - 20 - one - 21 - acetate yields 17b -methyl-18-nor- D 5,13-17a -pregnadiene-3b ,16a ,20, 21-tetrol 21-acetate.
GB2456/56A 1955-02-03 1956-01-25 New steroid compounds and method for the transformation of epoxy-ketones by the action of fermenting yeast Expired GB813317A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT813317X 1955-02-03

Publications (1)

Publication Number Publication Date
GB813317A true GB813317A (en) 1959-05-13

Family

ID=11317177

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2456/56A Expired GB813317A (en) 1955-02-03 1956-01-25 New steroid compounds and method for the transformation of epoxy-ketones by the action of fermenting yeast

Country Status (1)

Country Link
GB (1) GB813317A (en)

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