Lüthy, Christoph;
Schlatter, Hans‐Rudolf;
Graf, Walter
Steroide und Sexualhormone 254. Mitteilung [1] Synthetische Versuche in der Limonin‐Reihe III. Stereospezifische Alkoxy‐ und Dialkoxy‐Alkylierungen von 19‐Hydroxy‐testosteronacetat
You can manage bookmarks using lists, please log in to your user account for this.
Media type:
E-Article
Title:
Steroide und Sexualhormone 254. Mitteilung [1] Synthetische Versuche in der Limonin‐Reihe III. Stereospezifische Alkoxy‐ und Dialkoxy‐Alkylierungen von 19‐Hydroxy‐testosteronacetat
Contributor:
Lüthy, Christoph;
Schlatter, Hans‐Rudolf;
Graf, Walter
Description:
<jats:title>Abstract</jats:title><jats:p>Three different procedures for intramolecular alkoxy‐alkylation of 19‐hydroxy‐testosterone‐acetate (<jats:bold>4</jats:bold>) are described each yielding a mixture of two products monoalkylated either at position C(2), C(<jats:bold>4</jats:bold>) or C(6). In all cases the alkoxy groups are introduced stereospecifically from the β‐side. Treatment of <jats:bold>4</jats:bold> with I<jats:sub>2</jats:sub>/(CH<jats:sub>3</jats:sub>)<jats:sub>2</jats:sub>CO leads to 5 and 6. Reaction of <jats:bold>4</jats:bold> with HgCl<jats:sub>2</jats:sub>/ClCH<jats:sub>2</jats:sub>SCH<jats:sub>3</jats:sub> gives rise to <jats:bold>12</jats:bold> and <jats:bold>13</jats:bold> whereas treatment with HC(OCH<jats:sub>3</jats:sub>)<jats:sub>3</jats:sub>/CH<jats:sub>3</jats:sub>C<jats:sub><jats:bold>6</jats:bold></jats:sub>H<jats:sub><jats:bold>4</jats:bold></jats:sub>SO<jats:sub>3</jats:sub>H affords <jats:bold>15</jats:bold>, <jats:bold>16</jats:bold> and <jats:bold>17</jats:bold>.</jats:p>