Synthesis of various 18-substituted progesterones

Rae Ann M. Auel; Robert W. Freerksen; David S. Watt

doi:10.1016/0039-128X(78)90050-8

Synthesis of various 18-substituted progesterones

Rae Ann M. Auel, Robert W. Freerksen, David S. Watt

Molecular and Cellular Biochemistry

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

In order to test the potential biological activity of 18-substituted progesterones, 3,20-dioxo-4-pregnene-18-carbonitrile (1a) was converted to 3,20-dioxo-4-pregnene-18-carboxylic acid (1b) and methyl 3,20-dioxo-4-pregnene-18-carboxylate (1d) via a sequence of reactions involving an intramolecular hydrolysis of the 18-carbonitrile. Lithium aluminum hydride reduction of the bisethylene ketal derived from 1a furnished 18-aminomethyl-5-pregnene-3,20-dione 3,20-bisethylene ketal (8). Acetylation and hydrolysis furnished 18-acetamidomethyl-4-pregnene-3,20-dione (1f) and simple hydrolysis of 8 furnished 3'αH-5',6'-dihydro-2',19β-dimethyl-3-oxo-4-goneno [13,17-c]pyridine (9). None of the compounds exhibited any activity in Clauberg or anti-Clauberg tests.

Original language	English
Pages (from-to)	367-374
Number of pages	8
Journal	Steroids
Volume	31
Issue number	3
DOIs	https://doi.org/10.1016/0039-128X(78)90050-8
State	Published - Mar 1978

Bibliographical note

Funding Information:
We thank the National Institutes of Health (HD-6-2855 and GM-22978-02) for their generous financial support and G. D. Searle, Inc., for a gift of various steroids.

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Endocrinology
Pharmacology
Clinical Biochemistry
Organic Chemistry

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10.1016/0039-128X(78)90050-8

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title = "Synthesis of various 18-substituted progesterones",

abstract = "In order to test the potential biological activity of 18-substituted progesterones, 3,20-dioxo-4-pregnene-18-carbonitrile (1a) was converted to 3,20-dioxo-4-pregnene-18-carboxylic acid (1b) and methyl 3,20-dioxo-4-pregnene-18-carboxylate (1d) via a sequence of reactions involving an intramolecular hydrolysis of the 18-carbonitrile. Lithium aluminum hydride reduction of the bisethylene ketal derived from 1a furnished 18-aminomethyl-5-pregnene-3,20-dione 3,20-bisethylene ketal (8). Acetylation and hydrolysis furnished 18-acetamidomethyl-4-pregnene-3,20-dione (1f) and simple hydrolysis of 8 furnished 3'αH-5',6'-dihydro-2',19β-dimethyl-3-oxo-4-goneno [13,17-c]pyridine (9). None of the compounds exhibited any activity in Clauberg or anti-Clauberg tests.",

author = "Auel, {Rae Ann M.} and Freerksen, {Robert W.} and Watt, {David S.}",

note = "Funding Information: We thank the National Institutes of Health (HD-6-2855 and GM-22978-02) for their generous financial support and G. D. Searle, Inc., for a gift of various steroids.",

year = "1978",

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doi = "10.1016/0039-128X(78)90050-8",

language = "English",

volume = "31",

pages = "367--374",

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T1 - Synthesis of various 18-substituted progesterones

AU - Auel, Rae Ann M.

AU - Freerksen, Robert W.

AU - Watt, David S.

N1 - Funding Information: We thank the National Institutes of Health (HD-6-2855 and GM-22978-02) for their generous financial support and G. D. Searle, Inc., for a gift of various steroids.

PY - 1978/3

Y1 - 1978/3

N2 - In order to test the potential biological activity of 18-substituted progesterones, 3,20-dioxo-4-pregnene-18-carbonitrile (1a) was converted to 3,20-dioxo-4-pregnene-18-carboxylic acid (1b) and methyl 3,20-dioxo-4-pregnene-18-carboxylate (1d) via a sequence of reactions involving an intramolecular hydrolysis of the 18-carbonitrile. Lithium aluminum hydride reduction of the bisethylene ketal derived from 1a furnished 18-aminomethyl-5-pregnene-3,20-dione 3,20-bisethylene ketal (8). Acetylation and hydrolysis furnished 18-acetamidomethyl-4-pregnene-3,20-dione (1f) and simple hydrolysis of 8 furnished 3'αH-5',6'-dihydro-2',19β-dimethyl-3-oxo-4-goneno [13,17-c]pyridine (9). None of the compounds exhibited any activity in Clauberg or anti-Clauberg tests.

AB - In order to test the potential biological activity of 18-substituted progesterones, 3,20-dioxo-4-pregnene-18-carbonitrile (1a) was converted to 3,20-dioxo-4-pregnene-18-carboxylic acid (1b) and methyl 3,20-dioxo-4-pregnene-18-carboxylate (1d) via a sequence of reactions involving an intramolecular hydrolysis of the 18-carbonitrile. Lithium aluminum hydride reduction of the bisethylene ketal derived from 1a furnished 18-aminomethyl-5-pregnene-3,20-dione 3,20-bisethylene ketal (8). Acetylation and hydrolysis furnished 18-acetamidomethyl-4-pregnene-3,20-dione (1f) and simple hydrolysis of 8 furnished 3'αH-5',6'-dihydro-2',19β-dimethyl-3-oxo-4-goneno [13,17-c]pyridine (9). None of the compounds exhibited any activity in Clauberg or anti-Clauberg tests.

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U2 - 10.1016/0039-128X(78)90050-8

DO - 10.1016/0039-128X(78)90050-8

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AN - SCOPUS:0018241961

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VL - 31

SP - 367

EP - 374

JO - Steroids

JF - Steroids

IS - 3

ER -

Synthesis of various 18-substituted progesterones

Abstract

Bibliographical note

ASJC Scopus subject areas

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