N-Benzoyl-N-methylandrostan-17β-amines; 20-Aza Analogues of Brassinolide

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Title:N-Benzoyl-N-methylandrostan-17β-amines; 20-Aza Analogues of Brassinolide
Creators:
Slavíková, Barbora
Kasal, Alexander
Kohout, Ladislav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 5, pp. 655-661
Uncontrolled Keywords:<i>N</i>-Methylmorpholine <i>N</i>-oxide, <sup>1</sup>H NMR spectroscopy, Leuckart reaction, Steroids, Brassinosteroids, Aza steroids, Baeyer-Villiger oxidation

Abstract

3β-Hydroxyandrost-5-en-17-one (<strong>1</strong>) was converted into 17β-(<i>N</i>-methylamino)androst-5-en-3β-ol (<strong>4</strong>). In the corresponding <i>N</i>-benzamide <strong>5</strong>, structural features characteristic of brassinolide were produced in a standard way, <i>i.e. via</i> 3α,5α-cyclo derivatives <strong>7</strong> and <strong>8</strong>, ∆<sup>2</sup>-olefin <strong>9</strong> and 2α,3α-diol <strong>10</strong>. Baeyer-Villiger oxidation yielded two products: 2α,3α-dihydroxy-17β-<i>N</i>-(methylbenzamido)-7-oxa-7a-homo-5α-androstan-6-one (<strong>11</strong>) and 2α,3α-dihydroxy-17β-(<i>N</i>-methylbenzamido)-6-oxa-7a-homo-5α-androstan-7-one (<strong>12</strong>).

Title:N-Benzoyl-N-methylandrostan-17β-amines; 20-Aza Analogues of Brassinolide
Creators:
Slavíková, Barbora
Kasal, Alexander
Kohout, Ladislav
Uncontrolled Keywords:<i>N</i>-Methylmorpholine <i>N</i>-oxide, <sup>1</sup>H NMR spectroscopy, Leuckart reaction, Steroids, Brassinosteroids, Aza steroids, Baeyer-Villiger oxidation
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:63
Number:5
Page Range:pp. 655-661
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19980655UNSPECIFIED
ID Code:1331
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Slavíková, Barbora; Kasal, Alexander; Kohout, Ladislav (1998) N-Benzoyl-N-methylandrostan-17β-amines; 20-Aza Analogues of Brassinolide. Collection of Czechoslovak Chemical Communications, 63 (5). pp. 655-661. ISSN 0010-0765

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