Syntheses of (±)-17α- and (±)-17β-hydroxytacamonine; determination of configuration at C-17 |
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Authors: | David Din Belle Arto Tolvanen Mauri Lounasmaa |
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Institution: | David Din Belle, Arto Tolvanen,Mauri Lounasmaa* |
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Abstract: | Both (±)-17α-hydroxytacamonine (3) and its 17β-isomer (4) were synthesized in two steps (one-pot) from aldehyde mixture 5/6 via the cyanohydrin reaction. NMR spectral characterization of isomer 3 revealed it to be unidentical with natural 17-hydroxytacamonine, whereas spectral data of isomer 4 were in agreement with those published for the natural isomer. The configuration at C-17 was confirmed by NOE difference spectroscopy. |
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