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Photoinduced Isomerization of 23-Oxosapogenins: Conformational Analysis and Spectroscopic Characterization of 22-Isosapogenins

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https://figshare.com/articles/dataset/Photoinduced_Isomerization_of_23_Oxosapogenins_Conformational_Analysis_and_Spectroscopic_Characterization_of_22_Isosapogenins/2458066
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The first synthesis of 22-isospirostane derivatives is described. They were obtained by photochemical isomerization of 23-oxosapogenins. The structure of 23-oxo-22-isotigogenin acetate (12) was proved by a single crystal X-ray diffraction, while structures of 23-oxo-22-isodiosgenin acetate (13) and 23-oxo-22-isosarsasapogenin acetate (14) were elucidated by spectroscopic methods. 22-Isodiosgenin acetate (17) was obtained by NaBH4 reduction of the 23-oxo derivative 13 followed by the two-step Barton–McCombie deoxygenation procedure. Conformational analysis of 22-iso compounds was carried out with CD and NMR, as well as DFT calculations.
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2016-02-20
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