Studies on oxidation of ergot alkaloids: oxidation and desaturation of dihydrolysergol—stereochemical requirements |
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| Authors: | Radek Ga?ák Petr Sedmera Michaela Novotná |
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| Institution: | a Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ 14220 Prague 4, Czech Republic
b Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Venezian 21, 20133 Milano, Italy |
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| Abstract: | A new method for the oxidation of ergoline alcohols to aldehydes was found (TFFA-DMSO, −78 °C, then DIPEA). Structural features of ergolines required for successful C7-C8 double bond introduction via Polonovski-Potier reaction of respective 6-N-oxides were defined and experimentally confirmed: (i) the presence of electron-withdrawing group at C-8; (ii) trans-diaxial orientation of N6-O and C7-H bonds (both requirements are fulfilled for dihydrolyserg-17-al and its 2,4-dinitrophenyl hydrazone prepared in this work). |
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| Keywords: | Ergot alkaloids Lysergol Oxidation Desaturation Polonovski-Potier reaction |
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