6533b86ffe1ef96bd12cd0ac

RESEARCH PRODUCT

Partialsynthese neuer Ergolinderivate aus Clavinalkaloiden, 3. Mitt.1) O-Acyl- und O-Alkyl-1,6-dimethyl-8-hydroxymethyl-ergol-9-ene

E. Eich

subject

Indole testElymoclavinechemistry.chemical_classificationStereochemistryPharmaceutical ScienceEtherErgolinechemistry.chemical_compoundchemistryLysergolDrug DiscoverymedicineHydroxymethylAlkylmedicine.drugMethyl iodide

description

Elymoclavin (1), Lysergol (2) und O-Acyl-lysergole werden in flussigem Ammoniak mit Kalium und Methyliodid zunachst am Indolstickstoff methyliert. Durch Variation der Versuchsbedingungen werden 1 und 2 sekundar auch an der Hydroxylgruppe methyliert. Aus 1-Methyl-lysergol (3) sind daher nach der gleichen Methode mit verschiedenen Alkyliodiden 1-Methyl-lysergol-ether darstellbar. Dagegen gelingt die Ethersynthese nach Williamson aus 17-Halogen-ergolenen nicht. Partial Synthesis of New Ergoline Dervatives from Clavine Alkaloids, III: O-Acyl-and O-Alkyl-1,6-dimethyl-8-(hydroxymethyl)ergol-9-enes Elymoclavine (1), lysergole (2) and O-acyllysergoles are primarily methylated at the indole nitrogen when reacted with potassium and methyl iodide in ammonia. By variation of the reaction conditions, 1 and 2 can also be methylated at the hydroxy group. Thous, 1-methyl lysergole ethers can be prepared by the same method with different alkyl iodides. On the other hand, ether syntheses according to Williamson starting from 17-halogenoergolenes are not successful

https://doi.org/10.1002/ardp.19833160910