12,13-Epoxy-C-nor-D-homosteroids. VII. Reaction of 11-oxygenated 17.ALPHA.-acetyl-12.BETA.,13.BETA.-epoxy-13-epietiojervanes with boron trifluoride etherate and potassium hydroxide.
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概要
- 論文の詳細を見る
The title compounds were treated with boron trifluoride etherate in benzene at room temperature. 11β-Hydroxy- and 11-oxo-12β,13β-epoxides (<B>1</B> and <B>14</B>) underwent cleavage of the epoxy group at C-13 by the acid treatment to give the corresponding fluorohydrins (<B>2</B> and <B>5</B>) as the respective major products, while the former (<B>1</B>) also afforded a 13β-pregnane derivative (<B>3</B>) with a normal steroid skeleton. On the other hand, several 11-oxygenated 12α, 13α- and 12β,13β-epoxides (<B>17</B>, <B>17a</B>, <B>19</B>, <B>21</B>, <B>1</B>, and <B>23</B>) were treated with potassium hydroxide in aqueous methanol at room temperature. All epoxides gave the corresponding <I>Δ</I><SUP>13(17)</SUP>-20-ketones, and only 11-hydroxy- and 11-acetoxy-12α,13α-epoxides (<B>17</B>, <B>19</B>, and <B>17a</B>) were further transformed into a 13α-pregnane derivative (<B>12</B>).
- 公益社団法人 日本化学会の論文
著者
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Murai Akio
Department Of Chemistry Faculty Of Science Hokkaido University
-
Masamune Tadashi
Department Of Chemistry Faculty Of Science Hokkaido University
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Sasamori Hiroshi
Department of Chemistry, Faculty of Science, Hokkaido University
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