Structures and Synthesis of 4a-Homo-7,19-dinorsteroids, X-Ray Crystallography and NMR Spectroscopy

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Title:Structures and Synthesis of 4a-Homo-7,19-dinorsteroids, X-Ray Crystallography and NMR Spectroscopy
Creators:
Kasal, Alexander
Buděšínský, Miloš
Pelnař, Jan
Bruck, Michael A.
Brown, Michael F.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 12, pp. 2019-2034
Uncontrolled Keywords:Rearrangements, Absolute configuration, Antiandrogens, Conformation analysis, X-Ray diffraction, Steroids, NMR spectroscopy, <sup>1</sup>H, <sup>13</sup>C, Solvolysis

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. <p>

Title:Structures and Synthesis of 4a-Homo-7,19-dinorsteroids, X-Ray Crystallography and NMR Spectroscopy
Creators:
Kasal, Alexander
Buděšínský, Miloš
Pelnař, Jan
Bruck, Michael A.
Brown, Michael F.
Uncontrolled Keywords:Rearrangements, Absolute configuration, Antiandrogens, Conformation analysis, X-Ray diffraction, Steroids, NMR spectroscopy, <sup>1</sup>H, <sup>13</sup>C, Solvolysis
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:12
Page Range:pp. 2019-2034
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19992019UNSPECIFIED
ID Code:1613
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Kasal, Alexander; Buděšínský, Miloš; Pelnař, Jan; Bruck, Michael A.; Brown, Michael F. (1999) Structures and Synthesis of 4a-Homo-7,19-dinorsteroids, X-Ray Crystallography and NMR Spectroscopy. Collection of Czechoslovak Chemical Communications, 64 (12). pp. 2019-2034. ISSN 0010-0765

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