- Photo-induced Radical Rearragements 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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Irradiation of the hypoiodite of N-acetyljervine in benzene containing mercury (II) oxide and iodine gave a mixture of products.The major product was N-acetyl-11-oxojerva-5,12(13)-dien-3β-yl N-acetyl-A-homo-4-oxa-11-oxojerva-5,12(13)-dien-3α-yl ether (4) (25percent).Four minor products, N-acetyl-2-iodo-11-oxo-A-nor-2,3-secojerva-5,12(13)-dien-3-yl formate, N-acetyl-3α,5-epoxy-6α-iodo-A-homo-4-oxa-5α-jerva-5,12(13)-dien-11-one.N-acetyl-4-oxajerva-5,12(13)-dien-11-one, and N-acetyl-4-oxa-A-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 4.The formation of 4 as the major product contrasts with the result of the corresponding reaction of cholesterol.
- Suginome, Hiroshi,Kato, Kimitoshi,Masamune, Tadashi
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p. 3042 - 3047
(2007/10/02)
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