GB909261A - 18-oxygenated steroids and process for their synthesis - Google Patents

18-oxygenated steroids and process for their synthesis

Info

Publication number
GB909261A
GB909261A GB3931658A GB3931658A GB909261A GB 909261 A GB909261 A GB 909261A GB 3931658 A GB3931658 A GB 3931658A GB 3931658 A GB3931658 A GB 3931658A GB 909261 A GB909261 A GB 909261A
Authority
GB
United Kingdom
Prior art keywords
acetoxy
oxo
ketals
hydroxy
double bond
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
GB3931658A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB909261A publication Critical patent/GB909261A/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)
  • Steroid Compounds (AREA)

Abstract

The invention comprises compounds of the following formulae:-<FORM:0909261/IV (b)/1> (wherein R represents a free, esterified or etherified hydroxyl group) their 3-ketals, 11b -acetoxy-16,18-dioxoandrostane compounds and their ketals, particularly D 4-11b -acetoxy-13,16,18-trioxo-14-isoandrostene, D 5,14 - 3 - ethylenedioxy - 11b - acetoxy - 16,18 - dioxoandrostadiene, D 5-3-ethylenedioxy-11b -acetoxy-14,15-oxido - 16,18 - dioxoandrostene, also 11b - hydroxy-16,18-dioxoandrostane compounds, their free, esterified or etherified 18,11-cyclohemiacetals and their ketals, particularly D 4-3,16,18-trioxo - 11b - hydroxyandrostene, and 18,11-lactones of 11b -hydroxy-16-oxoandrostan-18-acids and their ketals, particularly the 18,11-lactones of D 5,14-3-ethylene-11b -hydroxy-16-oxo-androstadien-18-acid and D 5-3-ethylenedioxy - 11b - hydroxy-16-oxo-androsten-18-acid, together with a process for the preparation of 11,18-dioxygenated 16-oxo-androstane compounds by subjecting a D 4,18-3,16-dioxo-11b ,18a - oxido - 18a - methyl-18-homoandrostadiene of formula:- <FORM:0909261/IV (b)/2> which may contain a double bond in the 14,15-position, or a 3-ketal derivative, to oxidative cleavage of the 18,18a-double bond, e.g. by ozonisation and reductive cleavage of the ozonide, or hydroxylation and periodate splitting, the 11b -acetoxy group in the resulting 11b -acetoxy-18-oxo compound is hydrolysed in an alkaline medium, and if there is a 14,15-double bond, such bond or the 16-oxo group is temporarily protected and, if desired the resulting 18,11-cyclosemiacetal group is functionally converted and/or the 14,15-double bond is hydrogenated at any stage of the process. Detailed examples illustrate the invention and reference is made to further steps leading to a synthesis of aldosterone. Specifications 814,711, 893,577 and U.S.A. Specification 2,904,545 are referred to.
GB3931658A 1957-12-05 1958-12-05 18-oxygenated steroids and process for their synthesis Expired GB909261A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH5341157 1957-12-05

Publications (1)

Publication Number Publication Date
GB909261A true GB909261A (en) 1962-10-31

Family

ID=4518661

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3931658A Expired GB909261A (en) 1957-12-05 1958-12-05 18-oxygenated steroids and process for their synthesis

Country Status (2)

Country Link
ES (1) ES245655A1 (en)
GB (1) GB909261A (en)

Also Published As

Publication number Publication date
ES245655A1 (en) 1959-06-01

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