12,13-Epoxy-C-nor-D-homosteroids. VIII. Transformation of 12.ALPHA.,13.ALPHA.-epoxyetiojerv-5-ene-3,17-dione 3,3-ethylene acetal into testosterone.

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概要

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• Transformation of the title epoxy ketone (<B>2</B>) into testosterone (<B>1</B>), which implies synthesis of the hormone <B>1</B> from jervine, is described. Irradiation of <B>2</B> by a low-pressure lamp in dioxane afforded an androstane-12,17-dione derivative, which was reduced regioselectively with lithium tri-<I>t</I>-butoxyaluminium hydride to give 12β-hydroxy ketone (<B>5</B>). The compound <B>5</B> was transformed <I>via</I> a. four-step process into androstan-4-ene-3,17-dione, which was converted into <B>1</B> by a known procedure. The overall yield amounted to 1.8% from jervine.

• 公益社団法人 日本化学会の論文

著者

• Murai Akio

  Department Of Chemistry Faculty Of Science Hokkaido University

• Masamune Tadashi

  Department Of Chemistry Faculty Of Science Hokkaido University

• IWASA Noriaki

  Department of Gynecologic Oncology, Saitama Medical University, International Medical Center

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