Studies on oxidation of ergot alkaloids: oxidation and desaturation of dihydrolysergol—stereochemical requirements

Autor:	Daniele Passarella, Radek Gažák, Michaela Novotná, Bruno Danieli, Vladimír Křen, Petr Sedmera
Rok vydání:	2007
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Double bond chemistry Lysergol Organic Chemistry Drug Discovery medicine Organic chemistry Hydrazone Biochemistry Ergoline medicine.drug
Zdroj:	Tetrahedron. 63:10466-10478
ISSN:	0040-4020
DOI:	10.1016/j.tet.2007.07.099
Popis:	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).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::446966aa6889e9dad9a66967f3cc8fcc https://doi.org/10.1016/j.tet.2007.07.099 Zobrazit plný text záznamu Full Text from ScienceDirect