12,13-Epoxy-C-nor-D-homosteroids. III. The synthesis and stereochemistry of 17-oxygenated 12,13-epoxyetiojervanes.
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概要
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The synthesis of several 17-oxygenated 12,13-epoxyetiojervanes is described. Jervine (<B>1</B>) was degraded by a known procedure into trienone (<B>10</B>), which on hydride reduction afforded 11α- and 11β- alcohols (<B>11</B> and <B>12</B>). The respective alcohols were submitted to the Lemieux-Johnson oxidation to give <I>Δ</I><SUP>12</SUP>-17-oxo-11-alcohols (<B>13</B> and <B>14</B>), which were reduced under the Birch conditions to yield <I>Δ</I><SUP>12</SUP>-17-ketone (<B>15</B>). Epoxidation of these alcohols and ketone produced the aimed epoxides (<B>18</B>–<B>24</B>). The structure and configuration of these epoxides and the synthetic intermediates were determined on the basis of the chemical and spectral evidence.
- 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
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Takeda Masami
Department Of Biopharmaceutics Faculty Of Pharmaceutical Sciences Chiba University
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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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Iwasa Noriaki
Department of Chemistry, Faculty of Science, Hokkaido University
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