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Springer Fortschritte der Chemie Organischer Naturstoffe/Progress in the Chemistry of Organic Natural Products: 26

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Description

BARTON und COHEN haben r9S7 in einer Arbeit "Some Biogenetic Aspects of Phenol Oxidation" (3) Dienone der allgemeinen Formel (I) als biogenetische Vorstufen bestimmter Aporphin-Alkaloide postuliert (S. 260). Strukturen dieses Typs wurden erstmals r963 fUr die Alkaloide D-( +)-Pronuciferin und D-( +)-Crotonosin bewiesen [BERNAUER (II); HAYNES, STUART, BARTON und KIRBY (35)]. Der fur solche Verbin- dungen vorgeschlagene Sammelname "Proaporphine" (23, 65) bringt den in zwischen experimentell bewiesenen* biogenetischen Zusammenhang mit der Gruppe der Aporphin-Alkaloide zum Ausdruck, ist aber auch vom praparativ-chemischen Standpunkt sinnvoll, da sich Proaporphine (I) leicht in Aporphine (2) umwandeln lassen (S. 2S0). AuBer den Alkaloiden mit Dienongruppierung sind auch solche be- kannt geworden, in welchen eine oder mehrere Doppelbindungen des Dienonsystems aushydriert sind; sie werden sinnvollerweise den Pro- aporphinen zugerechnet. Dieser Aufsatz berucksichtigt alle natiirlichen Alkaloide und ihre wichtigsten Derivate sowie alle synthetischen Ver- bindungen, die das Skelett (3) besitzen (Tabellen I-3, SS. 270-279). Er macht ausschlieBlich von der in (3) angegebenen Bezifferung Gebrauch, welche der Nomenklatur der IUPAC und der Chemical Abstracts ent- spricht. Verbindung (I, R = H) ist wie folgt zu bezeichnen: 2',3',8',8'a-Tetra- hydro-S',6'-dihydroxy-spiro[2,S-cyclohexadien-r,7'(r'H)-cyclopent[ij]-iso- chinolin ]-4-on. R2 (2) K=H oder Alkyl (I) R=H oder Alkyl Rt=H,OH oder O-Alkyl Proaporphine Aporphine In den Originalarbeiten sind verschiedene, von der in (3) angegebenen ab- weichende Bezifferungsarten verwendet worden. Keine hat sich allgemein durch- gesetzt. Auch die von SLAViK (69) fur das sauerstofffreie Grundgerust der Pro- aporphine vorgeschlagene Bezeichnung Mecambran hat keinen Eingang in die Literatur gefunden.

Product Specifications

Format
paperback
Domain
Amazon UK
Publication Date
11 January 2012
Listed Since
21 December 2012

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