The Synthesis of an Etiojervane Analog of Corticosterone.

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概要

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• The synthesis of C-nor-D-homo-17-epicorticosterone 21-acetate (<B>1</B>) from jervine (<B>3</B>), which possesses the corticosterone configuration at each of the ring junctions, is described. Etiojerv-5-ene-3β,11β-diol-17-one (<B>4</B>), obtained by a seven-step process from <B>3</B>, was subjected to the Darzens reaction and afforded glycidic ester (<B>7</B>), which was converted by treatment with boron trifluoride into olefin (<B>9</B>). Catalytic hydrogenation followed by reduction with lithium aluminum hydride gave rise to tetraol (<B>15</B>), which was isolated as the acetonide (<B>16</B>). After Oppenauer oxidation of <B>16</B>, acid hydrolysis and subsequent partial acetylation, the resulting monoacetate (<B>19</B>) was oxidized with dicyclohexylcarbodiimide in dimethylsulfoxide to give compound <B>1</B>. Spectral and chemical evidence are presented for configurational assignment to both the compound and the synthetic intermediates.

• 公益社団法人 日本化学会の論文

著者

• Masamune Tadashi

  Department Of Chemistry Faculty Of Science Hokkaido University

• Orito Takako

  Department of Chemistry, Faculty of Science, Hokkaido University

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