Partialsynthese neuer Ergolinderivate aus Clavinalkaloiden, 4. Mitt. N‐1‐, C‐2‐ und N‐6‐monosubstituierte Agroclavine

Abstract

Agroclavin (1) wird in flussigem AmmoniaWKaliumamid mit Alkyliodid am Indolstickstoff alkyliert. 11aBt sich mit N-Iodsuccinimid zu 2-1od-1(3) urnsetzen. Mit der Bromcyan-Methode wird 6-Nor-1 (4b) gewonnen und danach an N-6 alkyliert.Pprtial SptbesM of New Ergoline Derivatives kom Chvine AIkdoids, I V Agroclavinee Monosobstituted at N-1, C-2, nnd N-6Agroclavine (1) is alkylated at the indole nitrogen with alkyl iodide in ammoniaipotassium amide. It is convertible to 2-iodo-l(3) with N-iodosuccinimide. Compound 6-nor4 can be prepared by means of the cyanogen bromide method; alkylation at N-6 is described exemplarily for the ethyl derivative.Fur Untersuchungen uber die Substratspezifitat der Agroclavinhydroxylase bei Cfavicepsfurifonnis2) und fiir pharmakologische Untersuchungen auf antibiotische') und zytostatische Wirkung4)wrden an den Positionen N-1, C-2 und N-6 variierte Derivate von 1 benotigt. Ober die Methyherung am Indolstickstoff der Claviaalkaloide 1, Elymoclavin und Lysergol wurde von uns bereits kiirzlich berichtet'). Analog erfolgte die Partialsynthese der Derivate 2a-2g durch Umsetzung von 1 in flussigem Ammoniak mit Kaliumamid und den entsprechenden Alkyliodiden (zu 2a, 2b, 2d, 2e, 2g

Microbiological C-17-Oxidation of Clavine Alkaloids, I. Substrate Specificity of Agroclavine Hydroxylase of Claviceps fusiformis

“…A modified sucrose-asparagine medium according to Brack et al (8) was employed. The preparation of the different substrates from 1 was already published by our team (9)(10)(11)(12), except five which were synthesized according to other authors (13)(14)(15). The partial synthesis of the corresponding derivatives of 2 is communicated in the present paper.…”

“…Synthesis of the substrates (derivatives of 1).-The synthesis of compounds 4a (9), 4b-4i, 5b, 7a, 7b (10), compound 6(11), and compound 9a (12) is already described elsewhere. Compounds 5a and 9b were prepared according to Yamatodani (13), 8 according to Hofmann et al (14), 10a and 10b according to Schreier (15).…”

(+)-Octen-l-yl-3-acetat aus dem etherischen Ö1 vonSenecio silvaticus

“…The microbiological and pharmacological activity of extracts of Chrysanthemum indicum L., small-flowered form (Compositae) was recently reported (1,2). In this connection we initiated a systematic chemical investigation of this poorly studied plant species (3)(4)(5). The essential oil and the petrol extract was found to consist mainly of mono-and sesquiterpene hydrocarbons and some their oxygenated derivatives (6,7).…”