A reductive elimination of steroidal diol monoesters with zinc giving the corresponding olefins.
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概要
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Steroidal <I>cis</I>-diol monoacetates (<B>1</B>,<B>9</B>,<B>11</B>, and <B>13</B>) were refluxed with zinc powder in acetic acid to give the corresponding olefins (<B>2</B>,<B>10</B>,<B>12</B>, and <B>14</B>) in good yield. Under the reaction conditions, no reaction occurred with diol diacetates (<B>1b</B>: R<SUB>1</SUB>=R<SUB>2</SUB>=H, R<SUB>3</SUB>=R<SUB>4</SUB>=Ac and <B>1m</B>: R<SUB>1</SUB>=C<SUB>6</SUB>H<SUB>5</SUB>, R<SUB>2</SUB>=H, R<SUB>3</SUB>=R<SUB>4</SUB>=Ac) and <I>trans</I>-diol monoacetates (<B>15</B> and <B>16</B>). Acyclic erythro and threo diol monoacetates (<B>17</B> and <B>19</B>) underwent highly stereoselective reduction affording <B>18</B> and <B>20</B>, respectively. The olefin-forming elimination proceeded with <I>syn</I>-elimination of a cyclic orthoacetate intermediate (<B>21</B>). The effect of some metals on the reduction and the behavior of a number of esters (<B>26</B>) and orthoesters (<B>27</B>) were also investigated.
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- A reductive elimination of steroidal diol monoesters with zinc giving the corresponding olefins.