A favorski reaction using iodosobenzene

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Abstract

Iodosobenzene or iodobenzene diacetate and excess base when reacted with 17β-hydroxy-5α-androstane-3-one (1a) unexpectedly gave a good yield of Favorski acid (3a) and some (3b). 17β-hydroxy-5α-19-norandrostan-3-one (1b) gave mainly the expected dimethylketal of the 2α-hydroxy-3-keto steroid (5).

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    Examination of the literature indicates that when iodine III compounds are employed, FR of cyclic ketones is only a deviation of the more generally observed α-hydroxylation-ketalization course (Scheme 3, Eq. 4) [18]. Daum described that treatment of 17β-hydroxy-19-nor-5α-androstan-3-one (9) with DIB/KOH in CH3OH led to a mixture of the 2α-hydroxy-3,3-dimethoxy ketal 10 as major product and only one the two possible regiosomers (11) resulting from A-ring contraction, (Scheme 3, Eq. 5) [19]. Additionally the same treatment of the ketone 12, led to the α-hydroxy-ketal 13 as the sole product [20].

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    Structure solution and refinement were carried out with the program(s): SHELXS97 and SHELXL97 [11]. Molecular graphics were generated with ORTEP-3 for Windows [12]; and the software used to prepare material for publication was WinGX [13]. Full-matrix least-squares refinement was carried out by minimizing (Fo2 − Fc2)2.

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