Photo-induced radical rearrangements of hypoiodite of N-acetyljervine and the related C-nor-D-homosteroid in the presence of mercury(II) oxide and iodine.

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概要

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• Irradiation of the hypoiodite of <I>N</I>-acetyljervine in benzene containing mercury(II) oxide and iodine gave a mixture of products. The major product was <I>N</I>-acetyl-11-oxojerva-5,12(13)-dien-3β-yl <I>N</I>-acetyl-<I>A</I>-homo-4-oxa-11-oxojerva-5,12(13)-dien-3α-yl ether (<B>4</B>) (25%). Four minor products, <I>N</I>-acetyl-2-iodo-11-oxo-<I>A</I>-nor-2,3-secojerva 5,12(13)-dien-3-yl formate, <I>N</I>-acetyl-3α,5-epoxy-6α-iodo-<I>A</I>-homo-4-oxa-5α-jerva-5,12(13)-dien-11-one, <I>N</I>-acetyl-4-oxajerva-5,12(13)-dien-11-one, and <I>N</I>-acetyl-4-oxa-<I>A</I>-homojerva-5,12(13)-diene-3,11-dione, were also isolated. Irradiation of the hypoiodite of 3β-hydroxy-17-ethyletiojerv-5-ene-11,20-dione also gave a dimer corresponding to <B>4</B>. The formation of <B>4</B> as the major product contrasts with the result of the corresponding reaction of cholesterol.

• 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

• Kato Kimitoshi

  Department of Chemistry, Faculty of Science

• Suginome Hiroshi

  Department of Chemistry, Faculty of Science

• Masamune Tadashi

  Department of Chemistry, Faculty of Science

• Suginome Hiroshi

  Department of Chemical Process Engineering, Faculty of Engineering, Hokkaido University

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