Effect of 11-oxygen function on the steric course of reduction of steroids by homogeneous catalytic hydrogenation

Yusuf J. Abul-Hajj

doi:10.1016/0039-128X(71)90043-2

Effect of 11-oxygen function on the steric course of reduction of steroids by homogeneous catalytic hydrogenation

Yusuf J. Abul-Hajj

Medicinal Chemistry

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

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Abstract

The effect of the 11-oxygen function on the stereochemieal course of homogeneous catalytic reduction of steroidal 1,4-dien-3-ones has been examined. Reduction of the 1,2-double bond in l,4-dien-3-ones using tristriphenylphosphinerhodium chloride as catalyst proceeds predominantly from the α-face except for the 11α-hydroxy substituted compound in which reduction is not stereospecific.

Original language	English (US)
Pages (from-to)	281-287
Number of pages	7
Journal	Steroids
Volume	18
Issue number	3
DOIs	https://doi.org/10.1016/0039-128X(71)90043-2
State	Published - Sep 1971

Keywords

1-dehydro-11-deoxycortisol = 17α, 21-dihydroxypregna-1,4-äiene-3,20-dione
1-dehydro-11-ketoprogesterone = 1-dehydro-11-oxoprogesterone = pregna-1,4-diene-3,11,20-trione
1-dehydro-llα-hydroxyprogesterone = 11α,-hydroxpregna-1,4-diene-3,20-dioiie
1-dehydrocortisol = 11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione
1-dehydrocortisone = 17α,21-dihydroxypregna-1,4-diene-3,11,20-trione.
1-dehydroprogesterone = pregna-1,4-diene-3,20-dione
11-deoxycortisol = 17α,21-dihydroxypregn-4-ene-3,20-dione
11-ketoprogesterone = pregn-4-ene-3,11,20-trione
11α-hydroxyprogesterone = 11α-hydroxypregn-4-ene-3,20-dione
11β-hydroxyprogesterone = 11β-hydroxpregn-4-ene-3,20-dione
Cortisol = 11β,17β,21-trihydroxpregn-4-ene-3,20-dione
Cortisone = 17α,21-dihydroxypregn-4-ene-3,11,20-trione
progesterone = pregn-4-ene-3, 20-dione

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@article{8eef418cc99f4e7aa1fb2d66f35742be,

title = "Effect of 11-oxygen function on the steric course of reduction of steroids by homogeneous catalytic hydrogenation",

abstract = "The effect of the 11-oxygen function on the stereochemieal course of homogeneous catalytic reduction of steroidal 1,4-dien-3-ones has been examined. Reduction of the 1,2-double bond in l,4-dien-3-ones using tristriphenylphosphinerhodium chloride as catalyst proceeds predominantly from the α-face except for the 11α-hydroxy substituted compound in which reduction is not stereospecific.",

keywords = "1-dehydro-11-deoxycortisol = 17α, 21-dihydroxypregna-1,4-{\"a}iene-3,20-dione, 1-dehydro-11-ketoprogesterone = 1-dehydro-11-oxoprogesterone = pregna-1,4-diene-3,11,20-trione, 1-dehydro-llα-hydroxyprogesterone = 11α,-hydroxpregna-1,4-diene-3,20-dioiie, 1-dehydrocortisol = 11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione, 1-dehydrocortisone = 17α,21-dihydroxypregna-1,4-diene-3,11,20-trione., 1-dehydroprogesterone = pregna-1,4-diene-3,20-dione, 11-deoxycortisol = 17α,21-dihydroxypregn-4-ene-3,20-dione, 11-ketoprogesterone = pregn-4-ene-3,11,20-trione, 11α-hydroxyprogesterone = 11α-hydroxypregn-4-ene-3,20-dione, 11β-hydroxyprogesterone = 11β-hydroxpregn-4-ene-3,20-dione, Cortisol = 11β,17β,21-trihydroxpregn-4-ene-3,20-dione, Cortisone = 17α,21-dihydroxypregn-4-ene-3,11,20-trione, progesterone = pregn-4-ene-3, 20-dione",

author = "Abul-Hajj, \{Yusuf J.\}",

year = "1971",

month = sep,

doi = "10.1016/0039-128X(71)90043-2",

language = "English (US)",

volume = "18",

pages = "281--287",

journal = "Steroids",

issn = "0039-128X",

publisher = "Elsevier Inc.",

number = "3",

}

TY - JOUR

T1 - Effect of 11-oxygen function on the steric course of reduction of steroids by homogeneous catalytic hydrogenation

AU - Abul-Hajj, Yusuf J.

PY - 1971/9

Y1 - 1971/9

N2 - The effect of the 11-oxygen function on the stereochemieal course of homogeneous catalytic reduction of steroidal 1,4-dien-3-ones has been examined. Reduction of the 1,2-double bond in l,4-dien-3-ones using tristriphenylphosphinerhodium chloride as catalyst proceeds predominantly from the α-face except for the 11α-hydroxy substituted compound in which reduction is not stereospecific.

AB - The effect of the 11-oxygen function on the stereochemieal course of homogeneous catalytic reduction of steroidal 1,4-dien-3-ones has been examined. Reduction of the 1,2-double bond in l,4-dien-3-ones using tristriphenylphosphinerhodium chloride as catalyst proceeds predominantly from the α-face except for the 11α-hydroxy substituted compound in which reduction is not stereospecific.

KW - 1-dehydro-11-deoxycortisol = 17α, 21-dihydroxypregna-1,4-äiene-3,20-dione

KW - 1-dehydro-11-ketoprogesterone = 1-dehydro-11-oxoprogesterone = pregna-1,4-diene-3,11,20-trione

KW - 1-dehydro-llα-hydroxyprogesterone = 11α,-hydroxpregna-1,4-diene-3,20-dioiie

KW - 1-dehydrocortisol = 11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione

KW - 1-dehydrocortisone = 17α,21-dihydroxypregna-1,4-diene-3,11,20-trione.

KW - 1-dehydroprogesterone = pregna-1,4-diene-3,20-dione

KW - 11-deoxycortisol = 17α,21-dihydroxypregn-4-ene-3,20-dione

KW - 11-ketoprogesterone = pregn-4-ene-3,11,20-trione

KW - 11α-hydroxyprogesterone = 11α-hydroxypregn-4-ene-3,20-dione

KW - 11β-hydroxyprogesterone = 11β-hydroxpregn-4-ene-3,20-dione

KW - Cortisol = 11β,17β,21-trihydroxpregn-4-ene-3,20-dione

KW - Cortisone = 17α,21-dihydroxypregn-4-ene-3,11,20-trione

KW - progesterone = pregn-4-ene-3, 20-dione

UR - https://www.scopus.com/pages/publications/0015116313

UR - https://www.scopus.com/pages/publications/0015116313#tab=citedBy

U2 - 10.1016/0039-128X(71)90043-2

DO - 10.1016/0039-128X(71)90043-2

M3 - Article

C2 - 5149003

AN - SCOPUS:0015116313

SN - 0039-128X

VL - 18

SP - 281

EP - 287

JO - Steroids

JF - Steroids

IS - 3

ER -

Effect of 11-oxygen function on the steric course of reduction of steroids by homogeneous catalytic hydrogenation

Abstract

Keywords

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