Structures and synthesis of 4a-homo-7,19-dinorsteroids, X-ray crystallography and NMR spectroscopy

Alexander Kasal; Miloš Buděšínský; Jan Pelnař; Michael A. Bruck; Michael F. Brown

doi:10.1135/cccc19992019

Structures and synthesis of 4a-homo-7,19-dinorsteroids, X-ray crystallography and NMR spectroscopy

Alexander Kasal, Miloš Buděšínský, Jan Pelnař, Michael A. Bruck, Michael F. Brown

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

2 Scopus citations

Abstract

X-Ray diffraction revealed the absolute configuration of 4aβ-methyl-4a-homo-7,19-dinor-5α,10α-androstane-3,17-dione. Detailed NMR analysis suggested that the 5α configuration existed in the starting material, 3β-acetoxy-4a-methylidene-4a-homo-7,19-dinor-5α-androst-9-en-17-one, and related compounds. Thus 5-methyl-5β-estr-9-ene derivatives with a leaving group in position 6β were found to react with nucleophiles to form rearranged 4a-homo-7,19-dinorandrostane derivatives with a 5α configuration.

Original language	English (US)
Pages (from-to)	2019-2034
Number of pages	16
Journal	Collection of Czechoslovak Chemical Communications
Volume	64
Issue number	12
DOIs	https://doi.org/10.1135/cccc19992019
State	Published - Dec 1999

Keywords

Absolute configuration
Antiandrogens
C
Conformation analysis
H
NMR Spectroscopy
Rearrangements
Solvolysis
Steroids
X-Ray diffraction

ASJC Scopus subject areas

General Chemistry

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10.1135/cccc19992019

Cite this

@article{816c40ee6d074de191c2d6d6dc88f012,

title = "Structures and synthesis of 4a-homo-7,19-dinorsteroids, X-ray crystallography and NMR spectroscopy",

abstract = "X-Ray diffraction revealed the absolute configuration of 4aβ-methyl-4a-homo-7,19-dinor-5α,10α-androstane-3,17-dione. Detailed NMR analysis suggested that the 5α configuration existed in the starting material, 3β-acetoxy-4a-methylidene-4a-homo-7,19-dinor-5α-androst-9-en-17-one, and related compounds. Thus 5-methyl-5β-estr-9-ene derivatives with a leaving group in position 6β were found to react with nucleophiles to form rearranged 4a-homo-7,19-dinorandrostane derivatives with a 5α configuration.",

keywords = "Absolute configuration, Antiandrogens, C, Conformation analysis, H, NMR Spectroscopy, Rearrangements, Solvolysis, Steroids, X-Ray diffraction",

author = "Alexander Kasal and Milo{\v s} Bud{\v e}{\v s}{\'i}nsk{\'y} and Jan Pelna{\v r} and Bruck, {Michael A.} and Brown, {Michael F.}",

year = "1999",

month = dec,

doi = "10.1135/cccc19992019",

language = "English (US)",

volume = "64",

pages = "2019--2034",

journal = "Collection of Czechoslovak Chemical Communications",

issn = "0010-0765",

publisher = "Wiley-VCH Verlag",

number = "12",

}

TY - JOUR

T1 - Structures and synthesis of 4a-homo-7,19-dinorsteroids, X-ray crystallography and NMR spectroscopy

AU - Kasal, Alexander

AU - Buděšínský, Miloš

AU - Pelnař, Jan

AU - Bruck, Michael A.

AU - Brown, Michael F.

PY - 1999/12

Y1 - 1999/12

N2 - X-Ray diffraction revealed the absolute configuration of 4aβ-methyl-4a-homo-7,19-dinor-5α,10α-androstane-3,17-dione. Detailed NMR analysis suggested that the 5α configuration existed in the starting material, 3β-acetoxy-4a-methylidene-4a-homo-7,19-dinor-5α-androst-9-en-17-one, and related compounds. Thus 5-methyl-5β-estr-9-ene derivatives with a leaving group in position 6β were found to react with nucleophiles to form rearranged 4a-homo-7,19-dinorandrostane derivatives with a 5α configuration.

AB - X-Ray diffraction revealed the absolute configuration of 4aβ-methyl-4a-homo-7,19-dinor-5α,10α-androstane-3,17-dione. Detailed NMR analysis suggested that the 5α configuration existed in the starting material, 3β-acetoxy-4a-methylidene-4a-homo-7,19-dinor-5α-androst-9-en-17-one, and related compounds. Thus 5-methyl-5β-estr-9-ene derivatives with a leaving group in position 6β were found to react with nucleophiles to form rearranged 4a-homo-7,19-dinorandrostane derivatives with a 5α configuration.

KW - Absolute configuration

KW - Antiandrogens

KW - C

KW - Conformation analysis

KW - H

KW - NMR Spectroscopy

KW - Rearrangements

KW - Solvolysis

KW - Steroids

KW - X-Ray diffraction

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UR - http://www.scopus.com/inward/citedby.url?scp=22844457363&partnerID=8YFLogxK

U2 - 10.1135/cccc19992019

DO - 10.1135/cccc19992019

M3 - Article

AN - SCOPUS:22844457363

SN - 0010-0765

VL - 64

SP - 2019

EP - 2034

JO - Collection of Czechoslovak Chemical Communications

JF - Collection of Czechoslovak Chemical Communications

IS - 12

ER -

Structures and synthesis of 4a-homo-7,19-dinorsteroids, X-ray crystallography and NMR spectroscopy

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 128199: Experimental Crystal Structure Determination

Cite this

Structures and synthesis of 4a-homo-7,19-dinorsteroids, X-ray crystallography and NMR spectroscopy

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 128199: Experimental Crystal Structure Determination

Cite this