Conrad Hans Eugster

Wirkstoffe aus dem Fliegenpilz

Der Fliegenpilz, A m a n i t a muscar ia (L. ex Fr.) HOOKER, ist niche nur dee seh6nste unserer GroBpilze, sondern auch dee bekanntes te . Leute, die sonst keine Prize sicher zu unterscheiden und benennen verm6gen, kennen wenigstens ihn. E r wird vielerorts geradezu als Symbol flit einen Giftpilz genommen. Giftig ist er ohne Zweifel, aber zum Tode ffihrt eine Fliegenpilzvergif tung nur ausnahmsweise. Der sehr viel giftigere und lebensgefghrliche Knollenbl~tterpilz, A m a n i t a phalloides (Vaill. ex Fr.) SEER., ist vergleichsweise viel weniger bekannt . Dieser merkwtirdige Sachverhal t mag daher rtihren, dab vielleicht heute noch Erinnerungsreste an eine ural te Verwendung des Fliegenpilzes zu Berauschungszwecken in brei ten Kreisen lebendig geblieben sind. Auch die h~iufige Erscheinung des Fliegenpilzes als Amule t t und Glfickssymbol, sowie in I l lustrat ionen zu gewissen MXrchen, deute t in dieselbe Richtung. Jedoch haben wir aus Europa keine einwandfreien Zeugnisse tiber den Gebrauch als psychotrope Droge in historischer Zeit. Bezeugt ist dieser jedoch mehrfach ftir sibirische Y61ker. Dee ~lteste und wohl bekanntes te Bef icht s t ammt yore schwedischen Offizier PHILIP JOHANN voN STRAHLENBERG (Stockholm t730), der seine Kriegsgefangenschaft zu einer Forschungsreise durch RuBland und Sibifien benutzen konnte. Er schrieb von den Koriaken:

Characterisation, chemistry and stereochemistry of carotenoids

Abstract - A review is presented on progress made since the 4th International Symposium on Carotenoids, Berne, Switzerland, 1975, in the following areas of carotenoid chemistry: – New structures. – Important chemical transformations. – Stereochemistry: new assignments of absolute configuration, and a chemists approach to a deeper understanding of the biological cyclisation step. – Carotenoids in rose flowers.

The identity of trollixanthin and trolliflor with neoxanthin

Abstract Trollixanthin and trolliflor have been shown to be identical with all- trans -neoxanthin from chromatographic and spectroscopic (visible, IR, NMR, mass, ORD and CD) evidence.

Bicyclo[3.3.1]nonanes as synthetic intermediates. Part 19.1 Asymmetric cleavage of ω-azabicyclo[3.n.1]alkan-3-ones at the ‘fork head’

Asymmetric cleavage of ω-azabicyclo[3.n.1]alkan-3-ones was achieved by asymmetric deprotonation at the ‘fork head’ ketone system with Koga’s chiral base and subsequent ozonolysis of the resulting chiral silyl enol ether to give the cis-α,α′-disubstituted piperidine, pyrrolidine and hexahydroazepine, respectively, in high enantiomeric excess.

Stereochemistry of Formation of theβ-Ring of Lycopene: Biosynthesis of (1R,1′R)-β,β-[16,16,16,16′,16′,16′-2H6]Carotene from [16,16,16,16′,16′,16′-2H6]Lycopene inFlavobacterium R 1560

Incubation of deuteriated precursors in cultures of Flavobacterium produced specifically deuteriated carotenoids. Analysis of these led to several conclusions: i) Lycopene is a direct precursor of β,β-carotene. ii) Its terminal Me groups retain their integrity during cyclization: there is a stereospecific folding of the 1,5-diene. The Me(16,16′) groups of lycopene become the Me(16,16′) of β,β-carotene. Consequently, the folding must follow the C2(E,E) mode. iii) Incorporation of deuterium was sufficiently extensive to permit CD measurements on the isolated β,β-carotene, allowing its centers of chirality to be assigned as (1S,1′S). iv) The same chirality resulted from incorporation of [2H3]mevalonate into zeaxanthin. The syntheses of specifically deuteriated [2H3]GPP, [2H3]FPP, and [2H3]GG are described.

Recent Progress in Carotenoid Structures

I am deeply moved by the great honour of being able to hold the Keynote-Lecture here and the introductory praise of my modest sucesses within the domain of carotenoids by Professor Liaaen-Jensen. I thank you all for this unusual award. In fact I am not at all certain whether I am really the most suitable person to be given such prominence for I know of other colleagues whose scientific results are internationally far better known than mine. Nevertheless I gladly accept this honour, above on because it concerns not just the man with pen and paper but rather more the coworkers at the front i.e. those at the laboratory bench. Moreover I can only hope that this tribute to a colleague, which has just been introduced by Norman for the first time, will be continued at a future carotenoid symposium.

NEW CAROTENOID STRUCTURES AND STEREOCHEMISTRY

Abstract A review is presented on progress made since the 5th International Symposium on Carotenoids, Madison, USA, 1978, in the following areas: – diastereo- and enantio-selectively deuterated carotenes and conformation of substituted ɛ-endgroups, – new carotenoids having ɛ-endgroups, – carotenes with vic. diolgroups, – carotene-5,6- and 5,8-epoxides, – structure of Z/E-isomeric carotenes and carotenoids, – chirality of selected carotenoids, – new findings on carotenoids from rose flowers.

Terpene und Terpenoide [Ohne Gibberelline)]

In den letzten Untergruppen sind die Verbindungen jeweils nach steigender Komplexitat des Kohlenstoffgerustes und bei gleichem Gerust nach steigender Anzahl der (formellen) C-C-Doppelbindungen, dann der konjugierten Doppelbindungen geordnet.

Synthesis and chiroptical properties of (1R,1′R)-[16,16,16,16′,16′,16′-2H6]-β,β-carotene

The title compound (3) has been prepared from dehydroabietic acid (1) in 21 steps and its low temperature c.d. spectra have been found to correspond to those for zeaxanthin (4) but with reduced intensities; possible interpretations of the observed c.d. spectrum are discussed.