The Synthesis of A-Homo-B-norandrostanes: The Effect of a Hydroxyl on the Course of Hydrogenation of the ∆9-Double Bond

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Title:The Synthesis of A-Homo-B-norandrostanes: The Effect of a Hydroxyl on the Course of Hydrogenation of the ∆9-Double Bond
Creators:
Kasal, Alexander
Slavíková, Barbora
Kohout, Ladislav
Buděšínský, Miloš
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 10, pp. 1631-1641
Uncontrolled Keywords:Hormone analogues, NOE experiments, Steroids, Steroid skeletal rearrangement, Ketone circular dichroism

Abstract

Acetolysis of 6β-mesyloxy-5-methyl-19-nor-5β-steroids (<i>e.g.</i> <strong>10</strong>) was proved to yield 4a-homo-7,19-dinor compounds (<i>e.g.</i> <strong>9</strong>) with a hydroxy group in the position 4aα. Hydrogenation of these compounds affords 9β,10β-dihydro derivatives (<i>e.g. </i><strong>12</strong>) predominantly, corresponding 9α,10α isomers (<i>e.g.</i> <strong>13</strong>) are only formed in low yields. This sequence was used for the synthesis of analogues of androgen hormones 4aα-hydroxy-4aβ-methyl-4a-homo-7,19-dinor-5α,9β,10β- androstane-3,17-dione (<strong>27</strong>), 4aα,17β-dihydroxy-4aβ,17α-dimethyl-4a-homo-7,19-dinor-5α,9β,10β-androstan-3-one (<strong>28</strong>) and 4aα,17β-dihydroxy-4aβ-methyl-4a-homo-7,19-dinor-5α,9β,10β-androstan-3-one (<strong>29</strong>).

Title:The Synthesis of A-Homo-B-norandrostanes: The Effect of a Hydroxyl on the Course of Hydrogenation of the ∆9-Double Bond
Creators:
Kasal, Alexander
Slavíková, Barbora
Kohout, Ladislav
Buděšínský, Miloš
Uncontrolled Keywords:Hormone analogues, NOE experiments, Steroids, Steroid skeletal rearrangement, Ketone circular dichroism
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:62
Number:10
Page Range:pp. 1631-1641
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19971631UNSPECIFIED
ID Code:1238
Item Type:Article
Deposited On:06 Feb 2009 17:07
Last Modified:06 Feb 2009 16:07

Citation

Kasal, Alexander; Slavíková, Barbora; Kohout, Ladislav; Buděšínský, Miloš (1997) The Synthesis of A-Homo-B-norandrostanes: The Effect of a Hydroxyl on the Course of Hydrogenation of the ∆9-Double Bond. Collection of Czechoslovak Chemical Communications, 62 (10). pp. 1631-1641. ISSN 0010-0765

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