Studies on oxidation of ergot alkaloids: oxidation and desaturation of dihydrolysergol—stereochemical requirements
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- 作者：Radek Gaž ; á ; k ; Vladimí ; r Kř ; en ; Petr Sedmera ; Daniele Passarella ; Michaela Novotná ; ; Bruno Danieli
- 关键词：Ergot alkaloids ; Lysergol ; Oxidation ; Desaturation ; Polonovski– ; Potier reaction
- 刊名：Tetrahedron
- 出版年：2007
- 出版时间：15 October 2007
- 年：2007
- 卷：63
- 期：42
- 页码：10466-10478
- 全文大小：554 K
文摘
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).