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Photoinduced Molecular Transformations. Part 132. A Two-Step Intramolecular Transposition of the 17β-Acetyl Group of Pregnan-20-one to C-18 through the Formation of Cyclobutanols by the Reaction of the Excited Carbonyl, followed by a Selective β-Scission of Alkoxyl Radicals generated..

DOI: 10.1039/P19920001843

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1843 - 1848 (1992)

Update date:2022-08-30

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Authors:

Suginome, HiroshiSuginome, Hiroshi

Nakayama, YutakaNakayama, Yutaka

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Article abstract of DOI:10.1039/P19920001843

New two-step transformations of a pregnan-20-one into 18-functionalized androstanes and 18a,18b-dihomoandrostanes are described; a type-II reaction of an excited pregnan-20-one protected in the A,B-ring gave the corresponding 20-hydroxy-18,20-cyclopregnane.Selective β-scission of the cyclobutanoxylradicals generated by irradiation of the nitrite or the hypoiodite gave a 5:4 ratio of the corresponding 18a,18b-dihomo-5α-androstane-18a-one and 18-iodoandrostan-17β-yl acetate in 89percent yield or 18a,18b-dihomo-5α-androstane-17,18a-dione 17-oxime in 83percent yield.The transformation involves a novel two-step intramolecular transposition of the 17β-acetyl group to C-18, and an oxygen insertion to the C-17-C-20 bond of pregnan-20 one.Several chemoselective transformations of the functional groups of the 18-iodoandrostan-17-one and 18a,18b-dihomo-5α-pregnan-18a-one, including the synthesis of 3β-hydroxy-18a,18b-dihomoandrost-5-ene-17,18a-dione, are reported.

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