GB679775A - Partial synthesis of progesterone - Google Patents

Partial synthesis of progesterone

Info

Publication number
GB679775A
GB679775A GB17853/50A GB1785350A GB679775A GB 679775 A GB679775 A GB 679775A GB 17853/50 A GB17853/50 A GB 17853/50A GB 1785350 A GB1785350 A GB 1785350A GB 679775 A GB679775 A GB 679775A
Authority
GB
United Kingdom
Prior art keywords
enol
ozonide
produce
progesterone
ester
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
GB17853/50A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB679775A publication Critical patent/GB679775A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
    • C07J53/002—Carbocyclic rings fused
    • C07J53/004—3 membered carbocyclic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

3 - Keto - bisnor - 4 - cholene - 22 - al, its 22 - enol esters and its 3 : 22-enol diesters are obtained by the following synthesis: stigmastadienone is treated with ozone to form the 22 : 23 ozonide thereof, which is reductively decomposed to produce 3-keto-bisnor-4-cholene-22-al, said aldehyde is esterified to produce a 22-enol ester or a 3 : 22-enol diester or a mixture of a 3 : 22-enol ester and a 22-enol ester, ozonizing said diester or a mixture of esters to produce an ozonide grouping in the 20 : 22 position, subjecting said ozonide to decomposition, hydrolysing the ester group in the 3-position of the product and isolating the progesterone thus produced. As esterifying agents there may be used carboxylic acid anhydrides.
GB17853/50A 1949-08-18 1950-07-17 Partial synthesis of progesterone Expired GB679775A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US679775XA 1949-08-18 1949-08-18

Publications (1)

Publication Number Publication Date
GB679775A true GB679775A (en) 1952-09-24

Family

ID=22079650

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17853/50A Expired GB679775A (en) 1949-08-18 1950-07-17 Partial synthesis of progesterone

Country Status (1)

Country Link
GB (1) GB679775A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102911232A (en) * 2012-11-02 2013-02-06 湖北丹江口丹澳医药化工有限公司 Progesterone preparation method

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102911232A (en) * 2012-11-02 2013-02-06 湖北丹江口丹澳医药化工有限公司 Progesterone preparation method
CN102911232B (en) * 2012-11-02 2015-03-11 湖北丹澳药业有限公司 Progesterone preparation method

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